


Standing There

by Anonymous



Category: Supernatural
Genre: Age Difference, Alternate Universe - Prostitution, Anal Fingering, Anal Sex, Angst, BDSM, Bondage, Brothels, Butt Plugs, Dom Castiel, Exhibitionism, F/M, Feathers & Featherplay, Femdom, Group Sex, Het, Loss of Virginity, M/M, MILFs, Mildly Dubious Consent, Multi, Office Sex, Panty Kink, Prostitution, Public Blow Jobs, Public Sex, Rimming, Safewords, Sex Worker Dean, Sex Worker Positivity, Sub Dean, Twink Dean
Language: English
Status: Completed
Published: 2014-07-29
Updated: 2015-01-20
Packaged: 2018-02-10 21:39:35
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 8
Words: 37,680
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2041197
Author URL: https://archiveofourown.org/
Summary: <blockquote class="userstuff">
              <p>"Katarina, mischievous grin spread across her face, reached up and gave Dean a peck on the cheek. With another harsh tap on the side of his jaw, she cooed, <i>'Good boy.'</i></p><p>And that was how Dean met his first pimp."</p><p>***</p><p>After the tragic death of his father, twenty year old Dean Winchester needs to prove to social services that he's fit to become his brother Sam's legal guardian. He's willing to do whatever it takes, even if it means becoming employed by a feisty Peruvian dominatrix, who introduces him to his first client, the mysterious Castiel.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Title based off of The Beatles' ["I Saw Her Standing There."](http://youtu.be/DsgWfAilIEM)

It was only fitting that rain began to fall just as the pallbearers lowered John Winchester into the ground.

Dean wrapped an arm around his younger brother, Sam, almost Dean's height already and growing, as their father used to say, "like a weed."

A knot bubbled up in his throat as he realized their father would never see Sam grow to his full height.

He leaned into Dean, staring silently ahead as the shiny black casket descended into its grave.

When everyone was gone– there weren't many people there to begin with– and rain began pouring down in large, fast droplets, Dean mumbled, "C'mon, Sammy. Let's go home."

***

A week after their father's funeral, Dean turned twenty years old. Instead of blowing out candles on a cake, Dean scanned through credit card offers, trying to figure out the damn difference between APR and APY and how much a five-thousand dollar balance on a twenty-five percent APR credit card would actually end up costing him.

Then he realized he didn't really have a choice.

McD's didn't pay the bills, even after he'd been promoted to shift leader. Picking up a second job cleaning offices at night didn't make ends meet. Then shoving in a third job between the cracks at Bobby's shop fixing cars whenever he got a free hour just wasn't doing the trick.

Dean didn't know what to do.

The last straw was underneath the pile of credit card offers, laying in wait to break the camel's back.

Dean picked up the innocent-looking envelope, addressed to him, and ripped it open, then scanned through the short letter.

He blinked, and read through it again.

Social services wanted to take Sam away, declaring Dean "unfit" to be his legal guardian.

In a fit of rage, Dean ripped up the letter. Then he ripped up the credit card offers. Then he punched a wall, right on a stud, and split three of his knuckles.

 _"Fuck_ social services," he seethed through clenched teeth. He punched the wall again, splitting a fourth knuckle. _"Fuck_ cancer." When he punched the wall a final time, blood smeared over the pristine, white plaster. _"Fuck my fucking life_." Then he leaned back against the wall and slid down it, looking up at the ceiling, silently praying to a god he didn't even believe in anymore to help him fix this fucked up situation.

***

Dean was at the shop when he met her.

It was a hot night in late July, so Dean kept the garage door up, letting in the last of the late evening light as the sun set on the horizon, dim and orange.

 _"Hola,”_ a woman's voice called from the side of a black Escalade.

Startled, Dean narrowly avoided bumping his head on the hood as he stood up straight.

The woman wore a short black halter dress covered in white polka dots, crazy curves in the form of a perfect hourglass, a wide-brimmed black hat atop a hair of black curls, and plush red lips twitching into a smile as she raked her eyes up and down Dean's body.

Dean wore his jumper, undone at the top and hanging around his waist, leaving his torso covered only in the thin white fabric of his undershirt, filthy with grease and motor oil, just like the rest of him.

As the woman's smile grew more devious by the second, she greeted him with a sultry, _"Buenos noches,”_ then paused to tilt her head and appraise him, adding in a subdued whisper, _"mi amor."_

"Hey?" Dean replied back, confused, having never been looked at like this woman was presently looking at him, her expression similar to Dean's whenever someone handed him a slice of pie.

Dean had never been anyone's pie before.

"Can I help you?" he asked.

When the woman didn't reply, opting instead to stare at him as though he were in a glass case, Dean added, "I'm sorry, I don't know Spanish."

"Are you a model?" the woman asked in a thick Spanish accent, big brown eyes widening and meeting Dean's for the first time, genuinely curious.

Dean huffed a laugh. "What? No."

She took a step closer to him, still appraising. "You are a very handsome man..." she trailed off, an invitation for Dean's name.

"Dean," he supplied.

 _"Dean_ ," she whispered in an exhale, as though knowing his name were a gift, then stepped close enough to him to place her hands on his shoulders and kiss one cheek, then the other. "I am Katarina. It is lovely to meet you."

He had no idea how to reply to that, and he was pretty sure she left lipstick coating both sides of his face. Still in her grasp, Dean swallowed and said, "I'm sorry, but we're closed."

She took a step back. "Oh. _Lo siento, mi amor_."

Dean shook his head. "Still don't know Spanish."

Katarina laughed, a lighthearted, giddy sound, in complete opposition to her deep, raspy voice, then said, "I came to see if my car was ready, but I see that it is not." She gestured to the Escalade.

Dean pointed to it. "This is yours?"

 _"Si,"_ Katarina replied, looking sheepish.

Dean had been taken off his game for a moment, but he got his footing back quickly, and leaned casually against the vehicle with a smirk on his face. "Wouldn't expect a pretty thing like you to drive such a beast."

Faster than Dean could process, Katarina pressed him against the side of the car, shoving her thigh between his legs, dangerously close to his family jewels, and lifted her hand to cup his face below his chin, bordering on choking him. Dean had to cross his eyes to see her clearly, and she dug her sharp red nails into his cheeks. _"Mi amor_ ," she began, voice deep and barely above a whisper, lips ghosting over Dean's, the scent of her floral perfume utterly intoxicating, "if you ever refer to me as a 'pretty thing' again, I will bend you over my knee and spank you until that beautiful young ass is the color of my lips."

Dean's jaw fell open and Katarina let go of him to gently press it back up and tap the side of his face, harder than necessary. "Do you understand?"

Dean nodded slowly, eyes wide.

"I want to hear you say it," she commanded.

"I understand."

She looked down and shook her head, a small giggle in her throat. Leaning in, she trailed her lips over the shell of Dean's ear, breath sweet and hot against the side of his face, and whispered, "I think you mean, _'I understand... Mistress.'_ "

Dean stared at her when she pulled away, a delighted smile etched across her tan features, perfect white teeth glinting in the waning light. Searching her eyes, Dean replied with a small nod, quiet and monotone, "I understand, Mistress."

Katarina, mischievous grin spread across her face, reached up and gave Dean a peck on the cheek. With another harsh tap on the side of his jaw, she cooed, _"Good boy."_

And that was how Dean met his first pimp.

***

"Are you sure this is safe?" Dean asked as Katarina shoved her fingers between the ropes and Dean's skin in several places.

Dean was tied up around a pole in a shady-looking building in a shady part of town, wrists, forearms, and upper arms tied tight behind him, the cool metal of the pole against his bare back and ass.

The old building, which may have once been a bed and breakfast, was filled with rooms remodeled to become what Katarina described as _"la casa de la diversión."_

He didn't ask what that meant.

Dean guessed he was in the penthouse suite, which had a king-size bed in it, topped with pristine white linens, and a pole from floor to ceiling in the center of the room, to which Dean was currently bound, in front of a large mirror spanning an entire wall. The lighting was modern, track lights in the ceiling dimmed to a peaceful yellow glow.

"Of course, _mi amor,"_ Katarina replied in a soothing lilt. "Castiel is one of my very good friends."

"By 'friend,' you mean 'client,' right?" Dean asked as Katarina circled around him, dressed in her trademark work uniform: a black bustier, lacy black thong, black thigh-highs, and black leather pumps, the only color on her body the warm dark tone of her skin, her bright red lips, and her chocolate brown eyes.

  _"Si,"_ she replied, walking over to a table and pulling various toys, bottles, and packages out of a large bag. "But my clients are my friends and my friends are my clients, _mi amor."_ She turned around, a black strip of satin in her hand, and added, "That is what you call 'good customer service.'"

Dean sighed. "I don't know why I let you talk me into this."

Katarina stepped close to him and ran a hand along his strong, sharp jaw. Dean leaned into the caress, missing the feel of a caring touch. Looking deep into his eyes, she whispered, "Because, Dean, you are a beautiful young man, and this world has not been kind to you. I cannot give you charity, but I can give you work so that you may keep custody of your brother. And I give you my best client, a very good friend of mine, who is also a beautiful man, and together we will take care of you the best we are able." She took a deep breath and combed her fingers through his hair, balling it into a fist and pulling at it until Dean hissed through gritted teeth. In a harsh growl, she concluded, "And we will make you feel _very good."_

Dean trembled, nervousness and anxiety coursing through his body.

Katarina lifted the blindfold to his eyes and tied it around his head. "Castiel is _very_ picky, and _very_ wealthy. He loves virgins, and when I told him about you, he offered to pay my highest price. I will give you your cut and a bonus if he agrees to see you again." She traced the pad of her thumb across Dean's lower lip. "I know he will. You are so good. The picture of innocence." She paused for a moment before asking, "Do you trust me, Dean?"

Dean nodded.

He could hear her smile when she whispered, "I want to hear you say it."

"Yes, Mistress," Dean mumbled.

She combed a soothing hand through his hair again, laying it flat from when she had ruffled it up. "Good boy," she cooed quietly, and added, "Have no fear, _mi amor_. I'll be listening in. I take good care of all my boys. I promise."

"Thank you, Mistress."

With a soft pat on the cheek, Dean heard the clicking of her stilettos as she left the room and closed the door behind her.

All there was left to do was wait.

***

Dean spent ten minutes freaking out, blind and tied to a pole, trusting what seemed to be a mildly sociopathic woman to protect him against someone he knew only as 'Castiel' which sounded like the fakest-ass name anyone could possibly come up with. He had no idea why he was doing this.

Right, he reminded himself. Sammy. Food. Shelter. Money.

He was selling his body for survival.

 _"The art of making someone feel loved is honest work,_ mi amor." Katarina's words to him on the topic reverberated through his head, soothing him slightly. _"Certainly more honest than feeding people processed, cancer-filled foods, no?"_

Her words stung, but he hadn't yet told her about the untimely demise of his father. Though she had a point, Dean admitted to himself.

If he could make money and prove that he was "fit" to be Sam's legal guardian while helping someone feel loved, Dean reasoned, then being tied up to a pole and blindfolded wasn't the worst thing he could be doing.

He took a deep breath, realizing he'd never been with a man before, never even _thought_ about being with a man before. He wasn't disgusted by the idea, but he wasn't thrilled by it, either.

When he was honest with himself, he was actually pretty grateful for the blindfold.

The door opened and Dean took in a sharp breath, body still trembling as he listened carefully to the door opening, dull padding of slow footsteps into the room. He held his breath as the door shut, and a deadbolt clicked over with a loud, ominous thud.

He reminded himself of the microphones, of Katarina right on the other side of them, listening for his safeword.

The footsteps walked closer to him and hesitated a few feet away. He heard shuffling as the man, Dean presumed, picked up the items Katarina left on the table and set them back down, huffing a breath of air that Dean hoped was a laugh.

Dean's instinct was to speak, but Katarina gave him the rules, and he was not to speak unless spoken to, so he stood there, surprisingly comfortable in his restraints but for being naked and exposed to a complete stranger whom he couldn't even see.

At last, the man spoke. "Hello, Dean." His voice was deep, and reminded Dean of running across a pebbled beach in bare feet. It was pleasant and intimidating, soft yet firm. Those two words sent a chill down Dean's spine.

Voice quivering, Dean replied, "H-hello."

A low chuckle rumbled in the man's throat. "You may call me Master."

Dean swallowed. "Hello, Master."

Footsteps paced in front of Dean, and he could feel the man's eyes on him, appraising him in much the way Katarina did when they first met. The man asked, flat, "How old are you?"

Katarina had told him to lie. "I just turned eighteen."

"Don't lie to me."

Dean's mind raced in a frantic attempt to think through everything Katarina had instructed him. At last he landed on a helpful bit of information: _"Do as you're told."_

"I'm twenty." For good measure, in case this displeased Castiel, he added, "...Master."

When the man stood still and silent, Dean added, "I just turned twenty last week, though."

The man remained silent, and the tension it created drove Dean insane. Nervousness getting the best of him, Dean asked, "How old are you?"

He heard a sharp intake of breath. "You may not ask me questions, Dean. Should you have any, you may direct them to your Mistress. If it's an urgent matter, you may safeword. Is this an urgent matter?"

Quietly, Dean replied, "No, Master."

"Remind me of your safeword. Your Mistress informed me, but I would like you to confirm it."

"Impala," Dean said, enunciating the syllables.

"Impala," the man mimicked back. "I promise I'll remember that." Then he hesitated before adding, "I will answer you, this one time, as long as you promise you understand. Do you understand?"

"Yes, Master."

The man paused briefly before replying, "I'm thirty-two."

Dean nodded, unsure how to respond, or even if he should.

"What do you say when your Master gives you something?" Castiel asked, a sudden sharpness in his tone.

 _Right_ , Dean thought. Katarina's rule _numero uno: "Be grateful."_

Her voice echoed in his head, reminding him that rule _numero sero_ was, _"Stay safe and sane."_

Dean began doubting the sanity of everything, however, the moment the Katarina stepped into his life.

"Thank you, Master," Dean whispered, his entire body shivering with a combination of trepidation and the cool breeze wafting into the room over his naked body.

"Good," Castiel replied, scooting a chair from the small table, legs screeching against the hardwood floor. The chair creaked as the man sat down.

"I must admit, you're not my usual type, Dean."

The tops of Dean's cheeks turned pink with the horror that he somehow already disappointed this man. He hung his head and replied, "I'm... I'm sorry."

Castiel was quick to correct him. "You misunderstand. It's not a bad thing. Just... different."

"Oh."

There was a short silence, until Castiel continued, "What do you do that makes you so... muscular? Do you exercise regularly?"

Dean wasn't sure how to answer, or how much information to give. "I... Not technically, no. Not... recreationally."

"Please elaborate."

"I'm active, I guess. I work on cars. I have two other jobs that require some heavy lifting. I used to play football in high school." He wished he hadn't said that last part.

"Are you in college?" Castiel asked.

And that was why. "No, Master. I didn't graduate high school." Dean cursed himself, having no idea why he felt the need to give this man more information than was strictly necessary to get the evening over with.

"Why not?"

Dean sighed. "My dad got sick, and I had to take care of him. He passed away a few weeks ago."

After a stunned pause, Castiel said, "I'm sorry to hear that, Dean."

Dean huffed a laugh. "Yeah, me too."

Silence hung in the air. "Have you ever been with anyone before?"

"Yes, Master."

"Elaborate, Dean. Men? Women? How many?"

This seemed like an invasive question, but Dean answered it nonetheless, because he supposed it was less personal than telling him he dropped out of school to take care of his dying father. "Seven women, no men."

Castiel chuckled. "Tell the truth, Dean. There's no reason to lie to me."

Dean swallowed audibly, wondering when the hell he became so transparent. "Two women." Rhonda Hurley, the girl he lost his virginity to when he was sixteen at a drunken party, and Lisa Braeden, his high school sweetheart, who left him when she couldn't handle his 'family issues' anymore. Then she went off to some college in Illinois and he hadn't heard from her since.

"Did you enjoy it?"

"Did I enjoy what?"

"Having sex with those two women."

"Well... yeah," Dean replied, relaxing for the first time in the comforting memory of waking up next to Lisa on one of their camping trips, naked in the middle of the woods on warm summer mornings. It felt like a whole other lifetime, like those memories had just been implanted in his head and weren't really his, and that it was impossible for something so simple and sweet to have ever occurred in his hellish life.

"Are you attracted to men?" Castiel asked.

Dean hesitated, mind at a complete standstill as he fought between the compulsive answer and the honest one. The compulsive answer was obviously, _"Fuck no, I ain't no queer,"_ just like his old man taught him, but seeing as how Dean was currently naked, blindfolded, and tied to a pole in a building owned by his pimp, he really didn't have much of a leg to stand on with the compulsive answer. Instead, he replied with the honest one: "I don't know."

He could hear the smile on the man's face when he responded, "Good answer."

The chair creaked as the man stood and took two short steps toward Dean, body heat enveloping his personal space. Dean was no longer comforted by his memories of Lisa as he was pulled abruptly back into the moment, back into this room with this man who wanted to do god-knows-what to him.

Dean felt a tug at the back of his head, and the blindfold slid off his face.

He looked up, blinking into the brightness of the room.

The man took a step back and let Dean gaze at him. His head tilted to the side and his eyes narrowed as he watched Dean watch him.

Castiel wore a black, well-tailored three-piece suit, lightly pinstriped, and a dark red tie. He was almost as tall as Dean, with a five o'clock shadow covering his strong jaw. His skin was nicely tanned and his eyes were the fiercest, brightest blue Dean had ever seen. His hair stood on end, crazy angles indicating to Dean the stress of a man who has to run his hands through it multiple times a day out of exhaustion or frustration or both. There was tufts of grey at the corners of his temples, and a couple shallow wrinkles in his forehead.

In all, Dean considered him an attractive man, but not one to whom he was particularly attracted, simply because he lacked the specific... _assets_ that generally drew Dean to another person.

When Dean was finally done appraising him, Castiel took off his jacket and slung it over the chair, then rolled up his sleeves to his elbows. He leaned down to reach into the breast pocket of his suit jacket, and pulled out two items.

Dean gaped.

In one hand, Castiel held up a long, black feather. In the other, he held a pair of silk pink panties with two little black bows on them. "Shall we begin?"

Dean gulped, and in a hesitant, nervous whisper, voice trembling, he replied, "Yes, Master."


	2. Chapter 2

**Notes for the Chapter:**

> OKAY, I HEAR YOU LOUD AND CLEAR. I'll continue this fic and try to devise some semblance of a plot to it.

Castiel was simply stunned by the boy in front of him. He had been expecting someone smaller, more fragile, lithe and pale.

Instead, Dean was all hard lines and sharp edges of functional muscle, tall and tanned.

Still, Cas could see the fragility within him. He understood why Katarina chose Dean to be his next plaything, why she spoke so highly of him, the bright, young, downtrodden virgin.

Castiel was all but drooling at the sight of him as they spoke. His arms were tied tightly behind him, stretching out his chest as he stood there, poorly balanced in every sense of the term. Whether he trembled in nervousness or excitement, Cas wasn't sure.

What Cas found most endearing about him, however, was his attitude. Not only did he obviously not know the ropes, he didn't know himself. He couldn't see himself the way Cas could see him. Dean was like an open book, and Castiel was eager to read every word on every page, and then maybe write a few of his own.

Dean stared at the items in Cas's hands, wide green eyes filled with apprehension.

Cas took a step closer to him and gently placed the long, black feather behind Dean's ear, then knelt down. "Step," he commanded, holding the panties out in front of him.

Dean stepped gingerly into one leg hole and then the next. The silk pink bikini-cut underwear was too small for him, but stretched around his muscular thighs easily enough as Cas slid them up his legs, tugging them over his bottom and then sliding his hands around to tuck the rest of him in, soft dick outlined against the shiny fabric.

Cas stepped back to look at his handiwork, trailing his eyes up and down Dean's body as the boy looked at Cas with an unreadable expression, obviously wanting to say something, but remaining silent per his instructions.

Cas stared him down until Dean looked away, blushing, then stepped toward him again, faces close together, and rose his hand above Dean's head to rest it on the pole.

Dean looked back up at him, searching his face.

Cas flicked his eyes down to Dean's lips, plush and soft and pink. His cheeks had just a ghost of stubble on them, and his face was completely bereft of blemishes but for a dusting of freckles across the bridge of his nose. The effect made him look more boyish than he already was, and Cas was sure he could stare at the beautiful constellations of those innocent freckles until their time was up.

He plucked the feather from behind Dean's ear and brushed it down the side of Dean's face. "Tell me, Dean," Cas said with a smirk, low and quiet, "are you a gambling man?"

When Dean spoke, his voice wavered. "No. I'm not old enough yet."

Cas's smirk broadened into a grin, and his dick twitched in his pants. He tilted his head to the side and, still grinning, asked, "Do you really want to be here right now?"

Dean froze, and Cas could see the gears turning behind his eyes, no doubt racing through the myriad of rules Katarina had shoved into his pretty little head.

"I give you permission to speak candidly, Dean," Cas assured him.

Dean swallowed, and looked away. "No, Master."

Cas touched the bottom of his chin with the feather, and Dean looked back up at him. "Where would you rather be?"

With a steady resolve, Dean replied, "At home. With my brother."

Cas nodded once. "That's fair. Shall we make a bet then, Dean?"

Dean blinked and gave a small gesture of his head for Cas to continue.

"I bet I can make you come without touching you." A confident smile covered his face as he took Dean's reaction in.

Dean scoffed. The corner of his mouth twitched up to reveal a small dimple on the side of his cheek, and Cas wanted nothing more than to lick it.

Patience, he reminded himself.

"There's no way," Dean replied with the shake of his head.

Cas shrugged, smiling. "What do you have to lose? You're already tied up."

"What are the terms?" Dean asked, a fierce glint in his eye that made Cas's stomach ache with want.

Trailing the feather down the center of Dean's chest, Cas replied, "If I can make you come without touching you, you have to see me, let's say, three more times. Here, like this. You'll still get paid, of course. If I can't, however, then I'll pay you for three more sessions, but you don't have to see me. You can stay home and be with your brother. How does that sound?"

Dean glared at him, silent for several moments before replying, "Deal."

***

Dean had never felt more like prey in his entire life. He wasn't one for making deals with people, but he figured he'd be doing this for a while anyway, so he really didn't have much to lose.

Money was money, and that's what Dean needed, much more than he needed an evening watching TV with Sammy.

Cas leaned in toward Dean's ear and spoke, breath hot against the side of his face. With a deep, even rumble, he began, "I'd like to tell you a story, Dean. Close your eyes."

Dean did, and braced himself for whatever Cas was about to tell him.

As Castiel spoke, he ran the feather all over Dean's torso, giving Dean chills over his skin and making him tense, hypersensitive to the long, bristly instrument.

"About ten years ago, I met Katarina at a burlesque club in New Orleans. She was a dancer back then, one of the most famous on Bourbon Street. I used to go there every night just to see her. The soft curves of her body, the beautiful tanned skin, her accent... She was the full package. When I finally got up the courage to talk to her, she looked at me like I was the only man in the world worth looking at. I know you know the look I'm talking about. Her big brown eyes just envelope you, take you in and see right through you at the same time, while that perfect red mouth coos uplifting words at you. It's heady, isn't it, Dean?"

As he asked the question, Castiel dusted the feather over Dean's dick. The light pressure of the touch coupled with the silky satin of the panties was a completely new feeling to him, and it felt so much better than he could have ever anticipated it would feel. It was tantalizing and frustrating, his cock only hardening fractionally at every word Cas spoke in his ear.

Hoarse, Dean whispered in reply, "Yes, Master."

"She took me home that night," Cas continued. "We drank wine in her apartment in the Garden District, windows open to the sticky Louisiana summer heat. She told me stories of Peru, about her travels, about a lifetime of sexual exploration that I couldn't even fathom. She was worlds above me. She's worlds above us all, Dean, don't let anyone tell you otherwise."

Cas flicked the feather back and forth across one of Dean's nipples, the small bud hardening more with every swish of the feather against it. Dean sucked his lip into his mouth and bit it, a pressure buzzing under his skin he'd never felt before, like an itch, but the solution wasn't to scratch, it was to touch and be touched, but he knew neither of those things would be happening tonight.

Dean opened his eyes when Cas didn't continue, watching his face examining Dean as he played with the feather over his skin.

Castiel gazed down at Dean's chest, nipples erect and cock half-hard. He chuckled at the sight, low and filthy, before continuing with his story. "When we finished our wine, I stood to take the glasses into the kitchen, and she followed me, taking me by surprise and pulling me down for a kiss. Have you kissed her yet, Dean? Has she let you? There's nothing in this world like it, that wide, hot mouth over yours, perfect white teeth biting at your lips. She hardly ever stops speaking, murmuring frantic Spanish between kisses, panting and always urging for more."

Dean could imagine it clearly. He'd been getting off to the memory of those lips for days now, orgasms ripping from his body as he imagined himself pressed against the side of her Escalade while she lowered herself to her knees and took him in her gorgeous mouth.

To Dean's dismay, he was fully hard now, cock straining against the elastic of the panties, tip peeking out the top, red and swollen.

Castiel lowered the feather to Dean's dick and traced it, from the base all the way up to the top. When it made contact with the head of his cock, Dean jolted and gasped, a bead of cum pearling at the tip.

Cas rolled the feather in it and then lifted it again to spread the cum across Dean's nipple, the cool wetness making Dean tense with that indescribable itch, which became more intense by the second.

"I'm sure you've figured out by now, Dean, that Katarina is not a woman of convention. She doesn't just take a man into her home to bed him. She aims to conquer the hearts, minds, and bodies of everyone she meets. She's like a queen in that way." Castiel huffed a laugh and continued, "So of course, after what felt like an eternity of passionate kissing, she sat on the kitchen counter and lifted her skirt for me. I was so eager, Dean. So eager to taste her, to shove my tongue up and down that beautiful cunt. It felt like a gift, letting me eat her out, hot pussy on my face while I circled my tongue around her clit, pressing two fingers into her. The only time she ever stops speaking is when she's about to come. All you have to do is keep circling her clit with light pressure, and press two fingers up into her g-spot, roll it around between them. She'll do the rest. She'll run her fingers in your hair and pull, direct you with patient instruction, and when she's silent, you'll know you've got her where you want her. You'll feel her walls clench over your fingers, and then she'll scream your name while her cum drips down your hand. Then she'll want to kiss you again, Dean. She'll pull you up and want to taste herself on you."

Dean's breathing became labored as the images from the story coupled with the feather ceaselessly trailing over his skin began unraveling his mind with want.

Cas removed his hand from above Dean's head and unbuckled his belt with long, deft fingers. Dean watched them and imagined them inside Katarina, expertly taking her apart. He wondered, briefly, what they would feel like on his cock, rock hard and begging to be touched.

He ripped off his belt with a snap and tossed it on the ground, then unbuttoned and unzipped his pants, and shoved his hand down them, stroking himself. Dean could see the slow, loose movements of his fist under his shirt, and his mouth watered, wanting to see more, wanting to feel those hands on him while simultaneously wanting Katarina too, and the effect was torturous.

Castiel ran the feather up and down Dean's dick in time with the jerks of his other hand on his cock, and stepped so close to Dean that he could feel the man's body heat radiating onto him, the smell of smoke and an early morning dollop of aftershave, the musk of masculine sweat an overwhelming combination to Dean's senses.

Cas's thigh was a mere two inches away from Dean's cock, easily within reach if Dean just took a step forward, stretching himself out. He could rub against Cas, relieve some of the immense tension flowing within him.

Voice an even deeper rasp, Castiel continued speaking, letting the occasional hitch of breath escape between his words. "After Katarina comes, she wants to be fucked. She wants to be fucked forever, until she comes again and again. That night, she pulled me between her legs and unbuttoned my pants, then guided me into her, precariously balanced on the countertop. She's hot and tight and perfect, legs wrapped around your waist... as you... fuck into her over and over. She won't let you come until she wants you to come. She has complete control of you, and she knows when to push you harder... She knows where your edges are and she throws you over them without ever letting you fall... She takes you apart..." Cas trailed off, fucking into his own fist faster and faster, wet slapping noises becoming louder as he let out a small moan.

Dean watched him, watched his face etched in pleasure, eyes closed and looking down as he thought of fucking Katarina, and a strong, unexpected, anger coursed through Dean's veins.

He wanted Cas to want _him_. That's why he was here. Because Cas was supposed to _want Dean_.

Dean's resolve broke, and he stepped forward, shoulders straining against his binds as he lined his cock up with Cas's thigh, rutting against it with abandon, reveling in the slick softness of the panties and the wetness leaking from him and onto Cas's pantleg.

Cas's eyes shot open and he dropped the feather, brining his hand up above Dean's head to steady himself onto the pole. He stared at Dean with blind urgency and shoved his thigh onto Dean harder, moving it up and down in time with his fist. His blue eyes darkened with lust as he gazed straight at Dean, and said, "Is this what you want, Dean?"

Panting, face etched in concentration as he thrust his hips onto Cas's leg like an animal, he could only reply with a small nod and a broken, high-pitched, "Uh huh."

The images flitting through his mind confused him. He was half imagining fucking Katarina in a kitchen and half imagining Castiel fucking _him_ in a kitchen. His thoughts battled it out as he stared into the stern, weary face of this man staring back at him, fucking his hand while watching Dean grind with abandon onto his hip, onto his suit that probably cost more than a month of Dean's rent, soiling the panties which rolled down his cock, the feel of the elastic and satin adding another layer of intense pleasure. At last, the image of being fucked by Cas won over, because more than anything, Dean wanted to be wanted by this man. He wanted to be touched by him and he wanted to touch back. He wanted Castiel to want him the way he wanted Katarina. He wanted to please him like Katarina pleased him.

"You wear your heart on your sleeve, Dean," Cas said, cheeks flushed pink with desire, words escaping between heavy breaths. "You want to come on this Armani suit. You want to mark me as yours. You want me to bend you over and take you. You want me to..." He leaned in and whispered in Dean's ear, lips so close but not touching that Dean was tempted to turn his head and kiss him just to break the tension, _"...touch you."_

Dean imagined Castiel's hands on him, all over him, his mouth kissing and licking every inch of Dean's body...

Then Cas's tongue darted out and traced the shell of Dean's ear, warm wetness sending an intense shiver down Dean's body that landed in his balls, tightening them, and, with one more filthy thrust onto Cas's thigh, he came with a shout, grinding down onto muscle below an expensive layer of fabric, satin slick with cum as he continued fucking out the waves of his orgasm, white hot ropes pulling from his body and running down Cas's hips and leg.

Castiel froze and took a deep breath, body jolting as he came into his fist with a gasp, silent but for a groan at the tail end of it.

When he stumbled backward and removed his hand from his pants, his lips were swollen and red, and his face was flushed. There was a large, wet, white stain on his thigh that dripped down the rest of his leg.

He stared at Dean for a long moment, breathless, expression completely unreadable.

Shaking himself out of the moment, Castiel took a towel from a drawer by the bed and cleaned himself off, then cleaned Dean off with the towel too, careful not to actually touch him.

Even though Dean just had an intense orgasm, that itch was still there, burning beneath his skin, yearning for the touch of those long fingers.

When Cas stepped away again, Dean, knees weak, slid down the length of the pole and slumped to the ground, knees to his chest.

Castiel straightened his tie, buttoned his pants, and put his belt back on. Then he lifted his suit jacket from its place on the chair, and folded it over his arm.

Without another look or word to Dean, as if Dean weren't even there, he left the room and shut the door behind him.

Something in Dean's chest fluttered and began to ache with a dull throb.

A cheerful sing-song voice filled the small room, and Dean looked up to find the source, eyes landing on a small speaker in the ceiling near the pole. "I will be there in a moment, _mi amor_."


	3. Chapter 3

**Notes for the Chapter:**

> This chapter happened because I rolled a d4 (I didn't have a coin on hand to flip). 
> 
> Because who needs plot or first-time sub drop when you can have an after-hours sexy Peruvian dominatrix to fix everything?

The door to the suite opened within a few moments, and Dean felt quick fingers untying the ropes over his wrists and arms. While undoing the last knot, a quiet, familiar voice said, "Bring your arms forward slowly, _mi amor_."

Dean did. His chest and shoulders burned as he wrapped his arms around his knees.

Katarina walked in front of him, then sat down on the ground cross-legged.

When Dean saw her, he did a double-take.

She was no longer wearing her elaborate lingerie, nor was she wearing a little black dress.

Instead, she was clad in a loose t-shirt and shorts, and her hair was up in a messy bun. She'd taken off all her makeup, so when she smiled at Dean, it was not with the red, luscious lips he was used to seeing, but with plush, pale ones.

"How are you feeling?" she asked, reaching out and stroking his arm, eyes wide with concern.

Dean looked her up and down. "Where's your whole...?" he asked, with a vague hand gesture over her torso.

"Oh." She glanced down at her faded Mickey Mouse t-shirt and black running shorts, then looked back up at him with a shrug and a crooked grin. "No more clients tonight."

"So, what? You just hole yourself up in a room somewhere and listen to people having sex?"

"And watch some, _si_ ," she replied with a nod. "It's good to be the boss."

"Wow," was the only response Dean could muster.

A short silence settled over them, and Dean was immediately brought back into the present moment, resting against a pole after being given an orgasm by a man with only a feather and a dirty mouth at his disposal, completely naked but for a pair of women's underwear, and sitting in front of his pimp who was wearing a Mickey Mouse t-shirt.

The fact that his fourteen year old brother was about to be taken away by Social Services if Dean didn't get his act together was so far away, he almost forgot about it. Dean felt like he was living someone else's life. It seemed like just yesterday he was playing three-man sandlot ball with his dad and brother in the heat of a random midsummer evening.

Now he was selling his body to a man who didn't even want to touch him anyway.

In not wanting to touch him, Dean _wanted_ to be touched by Castiel. He wanted it so bad that he humped the man's goddamn leg.

Dean felt used, and unwanted, and _filthy_.

Katarina scooted closer to him and wrapped her fingers around his hands, which were clutching his legs so tight that his knuckles turned white. "What's going on behind those beautiful green eyes, _mi amor_?"

Dean shrugged and rested his head on his knees.

She ran his fingers through his hair and spoke again, "Please talk to me, Dean. I cannot make this okay if you don't talk to me."

Muffled in his knees, Dean replied, "He didn't want me."

When Katarina didn't respond, Dean lifted his head to look at her.

Her eyes were wide and she held a fist over her mouth.

"What?" Dean asked.

Katarina burst out laughing.

 _"What?"_ Dean asked again.

She got on her knees and leaned in toward Dean, giggling and grinning, then placed her hands on either side of his face and kissed his forehead. "You oblivious, beautiful boy. I have known Castiel a very long time. Did you not hear his voice the way he spoke to you? Did you not see him orgasm from watching you orgasm? Did he not make a bet with you to see him three more times before you even began?"

Dean hadn't looked at it that way. "Well, yeah, but–"

"No buts. Let me tell you a secret..." She leaned in even further and rested her chin on his knees, grinning her amazing, bright white smile at him. Dean had to cross his eyes to see her properly. In a conspiratorial whisper, she continued, "Castiel very rarely comes."

"Really?" Dean asked. "Why?"

She shrugged. "Just his thing. He is a giving dom."

Dean was suddenly very aware of Katarina's soft, warm touch on his body. His palms began sweating and his heart sped up in his chest. Throat suddenly dry, he asked quietly, "What are you?"

Katarina grinned even wider and replied with a wink, "I am a taking dom."

Talking about doms and subs and power and kinks exhausted Dean. He didn't know sex could ever feel like his high school trigonometry class. It was overwhelming, learning all these new rules and being so close to Katarina. Dean took a deep breath, and stood up to walk over to the big bed, then crashed down on it, face-planting onto a pillow.

Katarina crawled into bed next to him and lay on her side, reaching out to rub consoling circles on his back. "Are you sure you are all right, _mi amor?_ What you did this evening I understand can be a very... jarring experience for a first time sub."

Dean rolled his head to the side and looked at Katarina, who stared at him with her big brown eyes, filled with sympathy and understanding.

He became unexpectedly overcome with a desire to give and be good for this woman who gave him this opportunity, who made him feel for the first time in his life that he was worth something, who was confident and beautiful and witty, and who smiled at him like there was nothing else in the world but the two of them. The way Castiel spoke of her made her seem larger than life, powerful, a force to be reckoned with. Dean wanted to feel her the way Castiel felt her. Dean wanted to listen to the words Castiel spoke in his ear over and over again as he felt them for himself. Dean wanted Katarina as much as he had wanted Castiel.

Before he knew what he was doing, Dean lifted himself up, then leaned forward, and pressed a light kiss to her lips.

She gasped and leaned back, bringing a hand up to her mouth. "Dean, you cannot do that."

"Why not?"

She stared up at him, brows furrowed. "Because it's against the rules."

Dean narrowed his eyes and gave her a crooked smile. "But you said yourself, _'ees good to be the boss,'"_ in his best impression of her accent.

Katarina continued looking up at him, searching his eyes, before lifting her hand up and threading her fingers through his hair, then bringing him back down for a searing kiss.

Castiel was right. Kissing Katarina was like nothing else. Her mouth was like a rich dessert, too much and not enough. It was so much to handle, it was suffocating, but Dean never wanted it to end.

Her lips tasted like cherry lip balm and her tongue was like sugar. She owned every second of the kiss, systematically exploring Dean's mouth with her own, her teeth nipping at him, her tongue sweeping across his upper lip and then his lower one. Between the deep kisses, she would pepper light ones at the corners of his lips while he was still reeling, trying to keep up with her.

It melted Dean's mind completely.

When Katarina abruptly pulled away, she looked at him with a stern glare, fingers still tangled in his hair. "I do not condone this behavior from my subs, Dean Winchester."

The corners of Dean's lips twitched up. "So why are you doing it?"

She yanked Dean's hair back, and with a shocking amount of strength and swiftness that he could barely comprehend, she flipped him on his back and straddled him.

"Because you are an insolent child who needs to be taught the rules."

Dean, coy smile across his lips, trailed a hand up the dark, smooth skin of her thigh, and looked up at her. "I'm happy to learn," he said, eyes wide with false innocence, and added, "...Mistress."

She smacked his hand away and leaned over him, bracing herself on the elaborate headboard while reaching up and pulling the hair tie out of the knotted bun at the back of her head with her other hand. Her hair tumbled down in long, dark waves. She leaned closer to his face and, when their lips were an inch apart, she growled, _"Bad_ _boy,"_ before closing the gap between them, kissing Dean with a level of fervor he had yet to experience in his short life.

Dean attempted trailing his hands up her thighs again, and this time she didn't smack them away, so he let them ghost over her voluptuous ass and up the drastic curve of her waist under her worn cotton t-shirt. Her skin was soft and hot under his fingers and he grasped at her with desperation, melting into her lips which were devouring him, owning him, teaching him and guiding him.

He didn't know he'd been doing something so simple as kissing so wrong, but now that he understood how to do it _right_ , it was a blissful act in and of itself, just as intense, if not more so, than all the sex he'd had in his life combined, which was fumbling and awkward by comparison to this, to being owned completely by this woman who was obviously the goddess of sex.

Dean didn't just _want_ Katarina.

He wanted to worship her.

Katarina sat up and dragged the t-shirt over her head, then tossed it to the side.

Dean stared at her breasts in awe, large and round, before sitting up and taking a nipple between his mouth, biting down on it.

Katarina hissed, and whispered, "Gentle, _mi amor_. Tease me. Do not torture me. That's my job."

He let up the pressure and teased it instead, which earned him a pleasant sigh. His dick twitched in his panties at the sound of it, and he moved to the other breast while bringing his hand up and fondling the first.

Katarina's hands never stopped moving over his body, her long nails trailing behind gentle fingertips over his back and neck and arms. Dean shivered when she hit some spots, and flinched when she lightly tickled at others. She was learning Dean's body by touch in a matter of moments, unyielding expertise at work.

She wrapped her legs around Dean's back and leaned backward on the bed.

Dean shifted so that he was on his knees between her legs, tiny running shorts bunched up around her thighs.

He leaned over her and trailed kisses down her throat, hand caressing the side of her delicate neck, biting and sucking his way down.

"No marks," Katarina reminded him, and Dean used only his lips from then on.

She reached up and took his hand from her neck, then pushed it into her shorts until Dean's fingers grazed her wetness.

He moaned, touching and toying at her entrance with his fingers, exploring her as she'd explored him, looking for all the spots that made her sigh and gasp in pleasure.

He slicked a finger in her wetness and pushed in, then followed with a second. Breaking away from her lips, Dean watched her face as he pulled his fingers out and circled them around her clit, just like Castiel had said to do.

Her eyes fluttered closed and she let out a low, quiet moan.

Dean grinned and swept another wide circle over the tiny, swollen bud.

Katarina bit her lower lip and groaned, _"Si, mi amor,_ _todo bien."_

Dean didn't need to know Spanish to understand her encouragement, so he did it again, and again, and Katarina continued mumbling incoherently between gasps and moans. He entered her with his fingers again, alternating between teasing her clit and pressing his fingers into her tight heat, until she whimpered a phrase Dean could understand, "Your mouth, _mi amor_. Give me your mouth."

He removed his hand from her shorts and gripped them by the waistband, pulling them off when Katarina arched her hips off the bed.

Dean's cock was hard and aching as he stared down at Katarina's naked body, all dark skin and wide hips, neatly trimmed hair between her legs. He kissed her once before moving down, lavishing her body with his mouth.

When he reached her navel, he noticed a horizontal, faded scar across her lower abdomen.

"You have kids?" he looked up and asked.

She nodded, _"Si. Dos."_

"You're a _mom?"_

Katarina opened her eyes and lifted her head to glare at Dean. "Yes. Is that a problem?"

Dean smirked. "No, it's just... now you're a MILF is all. It's hot."

She gave him an exasperated sigh. "Get to work, insolent child. I don't have all evening."

"Right," Dean replied with a grin. "Gotta get home to the kids."

Katarina threaded her fingers through Dean's hair and pushed his face down between her legs. "Do not make me punish you, _mi amor_. You will not enjoy my punishment."

Dean lifted his head away enough to mumble, "Yes, Mistress," before lapping his tongue up her slit.

The memory of Castiel's voice rumbled through his mind, his hot breath on the side of Dean's face, the feather ghosting up and down his cock, the vivid description of what Katarina liked.

Dean put two of his fingers in his mouth to wet before slowly entering her with them, then leaned down to tease her clit with his tongue.

He started slow; long, sure movements in and out of her soaking wet hole while he kissed and circled and teased her clit with his lips.

Among the quiet whispering in Spanish, Dean heard Katarina moan the words, _"Muy bien,"_ so he crooked his fingers up and grazed them down her upper wall, finding that large knot and stroking it.

Katarina gasped and arched off the bed.

Dean smiled and continued teasing her clit and g-spot at the same pace. He reached between his legs and palmed his own dick, rock hard and pressed against his stomach from the panties, elastic tight against the head of his cock. He stroked himself over top of them, still relishing in the feel of the silky fabric against his sensitive prick, tender from having come so hard only an hour ago.

Katarina's breathing quickened and she stopped speaking, stopped gently threading her fingers through his hair and guiding his head over her. Instead, she gripped his hair so hard that it hurt, and pressed his face onto her.

Dean sped up the pace and pressure of his fingers and tongue.

She was silent but for deep shuddering gasps and small jerks of her hips onto Dean's mouth, legs lifted and spread wide to give him the most access.

Dean rolled her g-spot between his fingers and pressed up while licking hard stripes over the tiny, hard nub.

Katarina took in a long sharp breath and held it.

He paused for a moment, keeping her at the precipice, before sweeping his tongue one more time, gently, over her clit.

She exhaled with a shout, bucking her hips up and arching off the bed completely, screaming Dean's name. Her walls clenched around his fingers and drenched them with her cum, pouring over his fingers and palm and wrist. He continued fucking her with his hand through her orgasm, following the flow of her waves as she rode them down, hips bucking up with every pulse while she moaned loudly in rapid half-Spanish, half-English, none of which Dean could understand.

At last, her orgasm died down and she sank onto the mattress, breathing deep.

Dean slowly removed his fingers from her before she gestured for him to come closer, and whispered, breathless, "Come here, Dean."

He crawled up her body and she pulled him in for a kiss, moaning into his mouth as she tasted herself on him. Then she pushed him away and looked into his eyes with an intense fire behind them. "Condom. Bedside table."

Hesitating, mind utterly fucking obliterated at the thought of not only going down on Katarina but fucking her too, she commanded, _"Now."_

Dean clambered across the bed and opened the drawer of the bedside table to pull out a condom. When he looked back, Katarina was on her knees, and instructed, "Lay down."

He lay back against the pillows and Katarina took the condom from him, tearing it open and popping it between her teeth before climbing between his legs and yanking the panties off of him in one rough, swift motion.

With sure hands, she stroked his dick, condom still precariously balanced on edge between her teeth, while she spread his cum down his shaft, quickly slicking it all over. Then she leaned down and rolled the latex over him, which was a completely new sensation for Dean, getting sheathed in a condom while being abruptly swallowed down.

If he hadn't already come once that night, there would be no way he could have gotten through the split second process of Katarina's lips over his dick without immediately spilling his load.

She climbed on top of him, straddling his waist, and gazed at him while she rubbed her wetness over his length.

When Dean trailed his hands up her thighs again, she grabbed his wrists and pinned them over his head with that unheard-of strength. Leaning down to his ear, lips grazing it, she whispered, "Do you want this, Dean?"

Dean nodded.

She positioned herself so that the head of Dean's cock was inside her, then pulled away and rubbed against him again.

"Are you _sure?"_

Dean nodded again, panting and straining against her.

"Insolent child," Katarina began, voice deep and raspy, accent thicker than usual, "I go to all this trouble to _teach_ you, and when I ask you a question, all you can do is nod? So impolite."

She reached down and flicked the head of his cock with her thumb.

Dean gasped, " _Yes_ , Mistress."

"Yes, what?"

She guided the tip of his prick into her and hesitated there.

He whimpered.

"Speak, boy. Tell me what you want."

"Please fuck me, Mistress," Dean groaned. _"Please."_

At last, she sank down the rest of the way on top of him, blissful tight heat enveloping him. His eyes fluttered closed and he impulsively bucked his hips upward.

She settled her weight on him. _"Ah ah ah_ ," she chided. "No cheating."

At an agonizingly slow pace, she lifted herself from him until he almost slipped out of her, then she sank down again. She swiveled her hips so Dean could feel every inch of her around him.

Dean was putty against her, offering everything for her to take, because all Dean wanted was to give, to worship, to show in any way his growing adoration for this woman who knew his body and his desires better than he did.

As she ground down on top of him, she leaned over him and asked, "Tell me, Dean. What did you think of Castiel?"

Mind blank, fuzzy with intense pleasure, Dean could only respond with a furrowed brow and a breathy, "Huh?"

"Castiel. Earlier this evening. Did you enjoy yourself with him?"

Dean wracked his brain to remember that anything existed outside of the present, beyond Katarina fucking herself onto him, slow and deep and perfect.

Then he remembered fierce blue eyes taking him in, owning him like Katarina owned him, but in a different way. He remembered the deep, gravelly voice and the vivid painting Castiel created with his words, reminiscent of this moment.

"Tell me, Dean. Tell me what he did to you," Katarina cooed in his ear before taking his earlobe between his teeth and biting down on it.

"He had this feather," Dean began between heavy breaths and quiet whimpers. "He kept... just... _teasing_ me with it. He told me about his first time with you."

 _"Si_. I heard that. What else?"

"He jerked himself off while watching me," Dean groaned as she sped up her thrusts on top of him and reached down with the hand not pining his wrists to rub her clit. A pressure built in him, but he stifled it down, knowing Katarina wasn't done yet.

"I would do the same. You are a lovely boy, _mi amor."_ She huffed a laugh in his ear, and Dean bucked up out of defiance.

A breath caught in her throat and she ground down on top of him again, forcing him deep inside her. She took his chin in hand and guided his attention to her stern glare. "I said no, Dean. Do not defy me again." She leaned down, and, without breaking eye contact, kissed him again, sucking his lower lip into her mouth. When she let go, she asked, "How did Castiel get you to come without touching you?"

The image of coming all over Castiel's suit flashed across his mind.

"I..." Dean trailed off, finding no way to tell the truth without admitting he had been desperate for the touch of a complete stranger. A complete _male_ stranger.

"Yes?" Katarina urged, rolling her hips in a slow circle. "Be honest with me, Dean, and you'll be rewarded."

Dean swallowed, and admitted, "I fucked his hip."

Katarina looked down at him with a wicked grin. "You're telling me you desired Castiel so much that you lost a bet just to get off against him?"

Dean squeezed his eyes shut, chest tightening and pressure building within him rapidly as the memory of Castiel coupled with the feel of being inside Katarina tore him apart. Through clenched teeth, he replied, "Yes."

"Are you attracted to him?"

Dean didn't respond.

"Answer me, Dean."

After a brief hesitation, Dean replied, "Yes, Mistress."

She leaned down and kissed him, smiling, then rumbled, "Good," against his lips.

Katarina thrust onto him harder, and Dean was balanced precariously at the edge. He bit down on his lip and strained against her vice-like grip on his wrists.

"Please, Mistress," Dean whimpered, writhing underneath her. "May I come?"

"Just a moment, _mi amor_ ," she replied, eyes closed, mouth hanging open as she worked at herself, deep in concentration. She looked up at him, and commanded, "Tell me you want Castiel to fuck you. Imagine it as vividly as you can, then say it aloud, and then you may come."

Dean imagined laying on his back like this, legs spread wide as Castiel stared down at him with those intense blue eyes, darkened with lust and want for Dean, fucking him open and taking him apart with the same expertise as Katarina. He imagined Castiel making him beg to be touched, making him beg for release, making him feel small and powerless and completely at his mercy.

With a rush of total honesty, Dean confessed, "I want Castiel to fuck me."

As soon as the last word left his lips, Katarina came again with sharp gasp, walls clenching around Dean as she fucked onto him harder and faster.

Dean instinctively bucked his hips up into her while imagining Castiel fucking into him at the same time, and he came, shouting, shoving into Katarina as she continued riding her orgasm downward. He filled her completely, shuddering up with jerks of his hips until at last they relaxed, and Katarina fell on top of him in a heap, letting go of his wrists and resting her head on his chest.

Panting, Katarina mumbled, _"Very_ good boy."


	4. Chapter 4

**Notes for the Chapter:**

> Normally I take longer to lead up to this (see: Dean Winchester Is a Gay Virgin), but I'm eager to get into the heavier kink. Enjoy some dom!POV.

Dean was wound up so tight that he couldn’t stop himself from trembling as he shed his clothes in the penthouse suite of Katarina’s _La Casa de la Diversión._

Katarina waited for him to finish folding them neatly and put them away in a drawer, like he’d been instructed.

He turned toward her and asked, “Now what?”

“Kneel at the end of the bed. I’ll put your blindfold on you.” Katarina was wearing what she referred to as her “uniform,” the characteristic lace bodice, thong, stockings, and high heels combo.

Dean raked his eyes up and down her body impulsively, and tried not to blush. Moreover, he tried to will his dick down, given that he had nothing to hide his insane attraction toward his pimp.

He climbed onto the mattress and sat back on his heels, then Katarina approached him and wrapped a blindfold around his head. “Why? What did Castiel ask for?”

“This is standard position, _mi amor._ Castiel did not text me this evening. I don’t know what you should expect.”

Dean swallowed audibly as his vision went black. “You have no idea?”

“None,” she replied, caressing the side of his face. “Don’t worry, though. You are in good hands.”

He reached up and held her hand on his face, leaning into her warm, welcome touch, reluctant for her to leave.

“You’ll be fine, _mi amor_ ,” she told him in a quiet, soothing tone, then leaned down and traced his bottom lip with her tongue, careful not to mark him with her bright red lipstick. Before pulling away, she whispered, “I promise.”

***

Castiel was a rational man.

Sometimes, though, he had bad days.

He worked in power games. He worked in the art of manipulation. It was his job to put criminals in prison, and he was very good at it.

But sometimes, he lost.

And the days he lost were his bad days.

Today, he lost.

It was the rape cases that made him the angriest. It didn’t matter how much evidence was stacked against these young men who took what they thought was theirs, the media always spun it so that the victim was at fault. The justice system was flawed, filled with _boys will be boys_ attitudes and _she was asking for it_ mentalities.

It made Cas _sick_.

Today, a young serial rapist went free. He didn’t even lose his scholarship. He got suspended from his classes with a slap on the wrist, a proverbial sly wink from the judge and the jury as they inferred that next time, he shouldn’t get caught.

Meanwhile, his client began the long path to emotional healing, potential years of inherent mistrust and therapy, adapting her behavior to her surroundings because her surroundings wouldn’t punish the perpetrator.

After a day like today, Castiel needed more than a drink.

He needed to fuck. He needed to feel an ounce of power in his oft powerless existence. He needed to give someone pleasure.

Cas opened the door to his favorite suite and gazed at the boy waiting for him there.

With an unexpected flutter of his heart in his chest, he realized that what he needed was Dean.

Silent, Cas stepped into the room and closed the door behind him, then took off his suit jacket and draped it across the chair.

He stared at Dean, who knelt at the foot of the bed completely still, hands on his knees and gazing downward, the only article on his body the blindfold around his eyes.

“Hello, Dean.”

Quiet, Dean replied, “Hello, Master.”

Normally, Castiel liked slowly taking his twinks apart. He liked getting to know them, their bodies, their kinks. He liked learning them and teaching them, piece by piece.

But this beautiful boy, perched so delicately on the edge of the large white bed, pristine skin taut against lithe muscle, pink lips pouting below dozens of faded freckles, pushed at the boundaries of Castiel’s willpower.

Today was just bad enough that Castiel lost his patience with his own resolve.

He stepped toward Dean and pulled at the knot tying the blindfold around his head, then tossed it aside.

Dean looked up at him, shy and surprised, blazing green eyes curious and nervous and a little bit scared.

Cas was frozen on the spot. All he could do was stare at Dean, completely overwhelmed by this pretty little slut, _his_ pretty little slut, to spend the next two hours with.

The possibilities were endless.

Because he hadn’t taken the time to push Dean’s buttons, to experiment with him, to categorize and file away all of the small noises and expressions Dean would make as Cas took him apart, Castiel asked him a question he’d never asked before, “What do you want?”

Dean’s mouth opened, hanging loose as he stared back at Castiel, unblinking. After a brief pause, Dean recited back the acceptable submissive response, “Whatever you want, Master.”

“Don’t bullshit me, Dean. I’ve had a long day. I don’t have time to guess. Tell me what you want.” Castiel took a step toward Dean and looked down at him. Dean had to crane his neck up to meet Cas’s gaze, the long line of his throat exposed to the soft yellow glow of the room.

Castiel wasn’t sure what he was expecting, but when Dean took a deep breath and replied with, “I want you to touch me,” Cas’s stomach did a little flip. 

It was such a simple request. No "blow me," or "let me go home." Just...  _touch me_. Out of everything Dean could have chosen, he just wanted to be touched. It was so...  _innocent_. 

Cas reveled in the bright red blush that spread over the boy’s body as he continued studying his dom, nervous yet defiant.

Something broke in Cas at that moment, and he threw all of his _usually_ s and _generally_ s out the window to cup Dean’s face in his hand, lean down, and meet their lips together.  

Dean tasted sweet and kissed as all boys did: sloppy, with too much aggression, but with wanton passion bursting at the seams. It was everything Cas loved about learning the bodies of young men, discovering what they craved without them yet knowing they craved it.

Dean moaned into Cas’s mouth and reached up instinctively to thread his fingers in his hair.

Castiel allowed it, allowed Dean to sit up on his knees so that Cas wasn’t bending down, allowed Dean to touch and explore with his hands and his tongue. Cas sucked Dean’s bottom lip and bit it gently, and it was like lighting a fire. Dean whimpered and pressed his young, naked body against Cas as tightly as he could, grasping onto him for dear life, like he was dying, drowning, and only Cas’s lips could save him.

At last, Cas broke away, holding Dean at the shoulders and pushing them apart.

Cas had to stifle the moan that almost escaped his lips when he looked at Dean, wild-eyed and wrecked, mouth swollen and red and spit-slicked. The blush that covered his body darkened, heat almost coming off of him in waves. His cock stood at attention, long and rigid, a pearl of cum at the tip threatening to drip down.

Reaching forward, Castiel thumbed at the bead of cum, barely crazing the tip of his dick, and brought it up to the boy's lips, smearing it across his filthy pink little mouth before shoving his thumb inside.

Dean met his gaze, green eyes dark and gazing at Cas through a fan of long lashes, and sucked on Cas’s thumb, sweet tongue swirling around the pad of it while he bit down gently around the joint.

Every ounce of Cas’s resolve completely shattered.

He pulled his thumb out of Dean’s mouth and reached down with both hands to grab the backs of his thighs and pull him forward, flipping him on his back and spreading his legs wide.

Dean grinned as Cas glared down at him, taking in the sight of Dean on his back, completely at the mercy of Cas’s will.

Castiel leaned down and ravaged his body in rough kisses, purposefully dragging the stubble of his five o’clock shadow around Dean’s flushed, sensitive skin. He bit and sucked and groped the boy, frantic and desperate, uncontrolled in a way Cas hadn’t felt in years.

Dean was a panting, trembling mess by the time Cas was done exploring his body with his lips. His cock repeatedly bobbed toward Cas, aching to be touched, but Cas ignored it, opting instead to suck one of Dean’s nipples into his mouth and bite down on it until Dean yelped.

Wrapping his lips around the other nipple, Castiel reached up and shoved two fingers into Dean’s hot mouth, watching Dean’s perfect little lips take his large fingers in.

Cas sat up, so hard in his pants that his belt stretched tight against the tip of his cock.

“Get on the ground,” Cas growled, removing his fingers from Dean’s mouth, and standing up to rip his tie away from his neck and toss it over his jacket.

When Dean stood, Cas pushed him down to his knees.

Dean watched him, looking up from his knelt position on the ground as Cas unbuttoned his shirt.

He stepped toward Dean, face inches away from the fly of his pants, and Dean glanced down at it.

Cas unbuckled his belt and slid it from his hips with a snap, then tossed it to the ground. He unbuttoned his pants and unzipped his fly as Dean stared at his crotch, wide-eyed and nervous.

“Reach behind your back and hold your left wrist with your right hand. Do not move them.”

“Yes, Master,” Dean replied, eyeing Cas’s hand which reached into his pants to stroke himself.

Cas pushed the fabric of his boxers down to the base of his dick. It fell forward, heavy and just an inch away from Dean’s mouth. “Jesus, Cas,” Dean whispered. “You’re... _huge.”_

Cas huffed a laugh, not commenting on Dean’s break from the scene, nor his newfound nickname, and touched himself as Dean watched, hands clasped behind his back as Cas instructed.

“You want to suck me, Dean?” Cas asked. “You want my huge cock in that pretty, filthy little mouth of yours?” Stepping closer, Cas rubbed his dick against the sharp line of Dean’s jaw, watching it graze the innocent freckles that peppered Dean’s young face.

Dean closed his eyes and leaned into it, then nodded.

Cas grabbed Dean by the hair and rubbed his cock against his mouth, back and forth, feeling those soft pink lips on the underside of his dick. Then he parted them and shoved himself inside, earning him a deep groan that reverberated through his prick and went straight to his balls, making him shudder in pleasure.

He was right in the assertion that Dean’s mouth was _filthy_. He took Cas in and swallowed him down immediately until Cas yanked the boy's head away by his hair and told him, “Stay still, you dirty little cumslut.”

Dean froze and Cas pummeled into his mouth again, the tight heat and blissful, light scrape of teeth against his dick sending shivers down his spine as he fucked Dean’s face with slow, steady thrusts.

Dean’s eyes watered when Cas hit the back of his throat, but he didn’t gag. Cas watched him writhe underneath him, breathing through his gag reflex, hitting the back of his throat again and staying there until Dean didn’t have a choice but to swallow, throat constricting at the head of Cas’s dick.

He pulled out and Dean heaved breaths, then he grabbed Dean back by the hair and shoved inside him again, grinding into his face with shallow stutters of his hips, trying to get deeper down his delicate little throat.

Dean looked up at him then, face beet red, tears streaming down his face, jaw close to unhinged around Cas’s giant cock, sweet lips wrapped around the base of it. He paused there for a moment before feeling Dean’s tongue snake up and down the underside of his dick, and Cas almost came right then, right down Dean’s throat.

He pulled out, gasping, and Dean bent forward to grab his throat and sputter; heavy, ragged breaths escaping him.

“Stand up,” Cas said, breathless, stepping away to pick up the lube and condoms Katarina left for him on the small table.

Dean stood, still panting, and Cas pressed his body against him, backing him up toward the end of the bed while reaching up and placing his hands around Dean’s throat, tilting it to the side so he could suck marks onto his collarbone.

When his knees hit the bed, Cas pushed him down on top of it and lifted his legs, folding him in half by the back of his knees. “Put your hands here and keep your legs open.”

Dean hooked his hands under his knees and spread himself wide for Cas.

Blatant fear was etched across his boyish features, like he was about to get punished for some immense wrongdoing.

It hit almost every item on Cas’s vast list of things that he found _really fucking hot_.

Cas let his gaze flicker up and down Dean’s body, soothing him by running a hand up the back of the boy’s thigh. He took a moment to steady himself, bring him back down to reality. Just because it was a scene and just because money was involved didn't make Dean an object for Cas to break because he had a bad day at the office. “It’s okay, Dean. Don't be scared, it won't hurt. Are you sure you want this?” Cas leaned down and kissed Dean's lips lightly, gently, feeling Dean's body relax underneath him. 

Dean gave a little nod, whispered, "Yes," so Cas uncapped the lid of the lube to coat his fingers with the cool gel.

He reached down and rubbed it up and down Dean’s crack, lightly, then circled his hole with the pad of his fingertip.

Dean’s eyes fluttered closed.

“Does that feel good?” Cas asked.

Dean nodded, and Cas felt him relax enough that he pressed his finger in, just up to the first joint. Gasping, Dean jerked in response.

Cas continued standing over him, rubbing his body with his other hand, even though he was burning with the desire to shove himself into the boy, balls-deep, _right fucking now._

“Have you ever done this before? To yourself?” Cas asked, pushing in to the second knuckle.

Dean, eyes clenched shut, shook his head.

“Would you like it if I touched you at the same time?”

Dean nodded, and Cas reached for Dean’s dick, still hard against his abdomen, cum pouring out of the tip and pooling onto his stomach.

Cas stroked the head of it with his thumb and Dean arched his back, inviting Cas’s finger deeper inside him. Cas grasped his cock in his palm and slicked it with cum, shiny with wetness and swollen, red and pretty and heavy in his hand.

He pulled his finger out and pushed it back in, then continued, timing the pressing of his fingers with the strokes of Dean’s dick in his palm.

When Dean began writhing underneath him, Cas inserted another finger, and Dean sucked a breath in through his teeth.

“Good or bad?” Cas asked, voice low and even, hiding to the best of his ability his unsteady resolve, slowly cracking under the surface.

“Good,” Dean gasped, then gasped again when Cas began scissoring his fingers inside him.

Cas kissed up and down Dean’s calf, biting at the warm flesh covered in fine hair, methodically opening Dean wide to fit his massive cock inside the tight virgin hole of this beautiful boy.

Dean’s breathing evened out and he relaxed around Cas’s relentless hands. Cas added a third finger, and Dean held his breath, gritting his teeth as he visibly willed himself to lower the tension in his body.

“Good,” Cas cooed, watching Dean’s face as he ran the gamut of the sexual spectrum, from pleasure to pain and back again, confusion and new feelings erupting over his divine features.

“Think you’re ready for me, Dean?” Cas asked, bending forward to bite down on Dean’s thigh. Dean moaned in response, clenching around Cas’s fingers, pulling him further in. Cas crooked them upward and gazed Dean’s prostate, and he shouted in surprise, arching completely off the bed and opening his eyes, blind with pleasure.

“What the _fuck_ was that?” Dean panted out, expression dazed.

Cas chuckled, low and dirty. “You mean this?” He pressed upward into it again and Dean screamed, spreading himself wider for Cas in the process. “That’s your prostate, Dean. What are schools teaching you these days?” Cas let go of Dean’s dick and slowly scissored his fingers wider, until he was sure Dean was thoroughly prepped. “Think you’re ready for me?”

Dean lifted his head off the bed and looked at Cas’s dick, still hard and hanging out of his pants. “You’re kidding me. There’s no way you can fit in me.”

Cas smirked. “Is that another bet?”

Dean shook his head.

“So are you ready?”

Letting his head back down on the bed with a huff, Dean replied, “I guess.”

 _Prissy little brat,_ Cas thought. He lifted his hand and slapped the back of Dean’s thigh, hard, leaving a red mark of his fingers in its wake.

Dean let out a yelp. “What was that for?”

“That was to remind you of your place. When I ask you a yes or no question, I want a yes or no answer.”

Dean swallowed, face flushing for a whole new reason, and replied, “Yes, I’m ready.”

“Yes, you’re ready, _what_?” Cas chided.

“Yes, I’m ready, _Master_ ,” Dean corrected.

“Good.” Cas picked up the condom and ripped open the package, then rolled the latex over himself and lined himself up to Dean’s hole. “Look at me while I enter you, Dean.”

Dean opened his eyes and stared into Cas, still young and ever-defiant. Cas rubbed against his entrance, circling the opening that was just begging to be filled, to be fucked wide open.

Dean squirmed underneath him as Cas toyed with him. “You want me inside you, you little cocktease? Want me to fuck you wide open? Fuck you until you can’t see straight?”

Breathing ragged, Dean stared at Cas and offered a high-pitched, “Uh huh.”

“You want to take my giant cock in your tight virgin ass?”

Dean bit his lip and nodded, innocent eyes wide with apprehension and anticipation.

Cas pressed in, just the head of his cock breaching the tight rim of Dean’s hole.

Dean breathed in a sharp breath, and Cas rubbed his hands over his legs, waiting for him to relax again.

When the ring of muscle loosened, Cas pushed in further, at the very edge of his resolve, biting back the urge to fuck into the virgin with abandon.

He pulled out a little, and stuttered his hips back in, pushing in further, a tiny bit at a time, until he was at last completely bottomed out, balls-deep inside him.

Dean let out a loud moan, and twitched his hips, inviting Cas to move.

Cas pulled out and pushed back in again, eliciting a cracked moan which escaped from Dean’s lips.

He continued to pump into Dean with slow, shallow thrusts, until Dean whimpered, “Please, Master, fuck me harder.”

For the second time that night, Castiel’s carefully constructed visage of control not only shattered, but burst into flame as he shoved into Dean, hard and fast, snapping his hips with steady, deep thrusts repeatedly.

He leaned over Dean and wrapped his arms around his back, grinding into his ass as deep as he could go, breathing heavy, dragging his lips across every expanse of skin he could reach, biting and sucking, clawing with his hands as he pounded into the boy’s ass relentlessly, fucking him wide open.

“Wrap your arms and legs around me,” Cas mumbled into Dean’s neck. “Hold on tight.”

When Dean did, Cas lifted him off the bed, and Dean sunk deeper onto his cock as Cas stood.

Despite Dean’s size, he was light as air, and Cas had no trouble standing in the middle of the room, arms wrapped tight against the sweaty, writhing body of the boy holding onto him, driving up into him until Dean was bouncing up and down on his hips.

Cas snaked his arm up and threaded his fingers in Dean’s hair, pulling back so that his beautiful throat was exposed, and Cas sucked on his pulse, feeling the speed of it between his lips, faint fluttering of Dean’s pleasure in Cas’s mouth.

“Grab the canopy,” Cas commanded, and Dean reached up to grab the wooden bar above him with both hands.

Cas swept his arms under Dean’s legs and spread him wide as Dean dangled from the canopy of the bed.

Grinding up into him, Dean’s cock slid between them, throbbing and slick against their abdomens.

Dean was beyond words, beyond sounds, as he gasped and held on for dear life.

Cas changed the angle of his hips and drove into Dean’s prostate, grazing it with the head of his cock, and Dean’s head lolled back.

“You like that?” Cas asked through gritted teeth. “You like me hitting that sweet spot, you fucking cockslut? You like your tight little ass getting fucked wide open? God, Dean, you’re such a pretty thing, all freckles and blushing, loving the feel of my cock in your little virgin hole.”

 He pounded into Dean, grazing his prostate again and again, until Dean’s arms were shaking with the weight of holding himself up.

Dean whined and keened and cried out against the speed and harshness of Cas’s unrelenting thrusts. “Gonna answer me, filthy slut? Do you love my dick up your ass or not?”

Dean shut his eyes tight and nodded.

Cas felt the pressure building in him, an odd feeling given his history of orgasm deprivation, but with this boy, he wasn’t going to deprive himself a goddamn thing. He was going to fill Dean up, and fuck him as many times as Dean would let him. Cas was willing to open his wallet wide if Dean was willing to open himself wide for Cas in turn.

“Yes, M-Master,” Dean stuttered between heaving breaths. “I love it.”

Cas lost all rhythm of his hips, thrusting erratically into Dean.

Dean swallowed and continued, “I love your massive fucking cock in my ass.”

Hearing that beautiful, pink little mouth speak those filthy fucking words was all it took to push Cas over the edge.

Dean screamed Cas’s name as he came, white hot stripes coating their stomachs and chests, and he let go of the bar. They toppled forward onto the bed, and with one final thrust, Cas came inside him, rolling his hips as deep as they would go, fucking into him hard and fast as he rode out the waves of his orgasm.

He slowed to a halt as the last jolts of pleasure were pulled from him, still buried deep inside Dean’s ass, then collapsed on top of him.

After he caught his breath, he lifted his arm and checked his watch.

They still had an hour.

Cas gently removed himself from Dean, then stood to pull his shirt from his shoulders and shove his pants off, which had fallen around his ankles. He walked over to the dresser and retrieved a towel, then went into the bathroom to wet it with warm water, and returned to clean Dean up.

He removed the condom from himself and tossed it in a trash can, then wiped himself down too.

Dean watched the whole routine with interest, propped up on his elbows, waiting to be spoken to so he could speak.

Cas stared down at Dean, let his eyes rake over his beautiful naked body, crimson flush finally abating.

Coming to a conclusion, Cas nodded to himself, and said, “So you wanted to be touched, right?”

Dean gave a slight nod, looking inexplicably ashamed of such a simple request.

Cas crawled into bed beside Dean, and guided him gently onto his side so that his back was Cas’s chest, then wrapped his arm around the boy’s midsection and curled around him. When he noticed Dean was shivering, he reached down to the end of the bed and covered their bodies with the thick down comforter.

He peppered Dean’s freckled shoulders with light kisses, grazing the soft skin with his lips, reveling in Dean’s small, pleasured sighs.

“Don’t get any ideas,” Cas whispered, murmuring into Dean’s skin. “Today was just a bad day. I don’t normally do this.”

“What happened?” Dean asked, voice quiet and muffled in the pillow by his head, slurred with drowsiness. Then he turned around in Cas’s embrace and stared up at him, faces close, looking at Cas with openness and honesty and innocence.

Castiel opened his mouth to reply, then realized no one really asked him about work, or why he had a bad day. There was no one to share in the burden of his cases, no one to come home to who would console him and tell him he was actually the good guy, no one to give pleasure to or make happy.

Like the rest of the evening, Cas broke another of his rules, and told Dean about his bad day, leaving out the pertinent information, mostly recounting how shitty it felt to lose such an important case.

Dean didn’t fall asleep. He listened politely and nodded, asked questions here and there. Their last hour came and went. Katarina didn’t interrupt them when their time was up, so Cas asked Dean if he would like to leave, and Dean shook his head. He continued talking until at last he felt better, free of the burden of his immensely shitty day, and they fell asleep together, tangled in each other’s embrace.


	5. Chapter 5

**Notes for the Chapter:**

> Sorry for the delay in updating this fic! As an apology, have a 5k word chapter of mild plot development followed by my favorite kind of smut.

Dean stood in front of the mirror, frowning as he held the ends of his necktie in each hand.

He had no idea how to tie a tie. His dad always did that for him.

 _"Dean!"_ Sam shouted from the living room. "We gotta go! We're gonna be late for our appointment with Naomi!"

"Just a minute!" Dean called back.

He wished he could afford Internet so that he could look up how to do it. When he tried once more, the tie ended up loose and backwards around his neck, so he gave up with a sigh and untied it, then dropped it back on his bed, which was really just a twin-sized air mattress.

They lived in a one-bedroom apartment on the bad side of town because that was all Dean could afford after his father passed. He'd sold his dad's king-sized bed for two hundred dollars, and his own twin-sized bed for one hundred. Sammy offered to sell his too, but Dean wouldn't let him.

Dean slept on the floor for a long time until he spotted an air mattress at a garage sale for five dollars and bought it, then felt immediately guilty when he realized that five dollars could buy them an entire day's worth of food. It seemed like a selfish purchase, but Sam threw a fit when Dean tried to return it.

So he had an air mattress now, which wasn't nearly as nice as the giant bed in Katarina's place, but sometimes, when he couldn't sleep and Sammy was snoring lightly on the opposite side of the room, he liked to close his eyes and remember his last night with Cas, how it felt to be held by someone he inexplicably trusted, who understood how to navigate the ridiculous maze of adult life in a way that Dean hadn't yet mastered. He had felt safe, and adored, and... happy.

It'd been two weeks since that night, and as each day passed without a text from Katarina, Dean became increasingly nervous that he'd freaked Cas out, because the next morning when he woke up, Cas had gone without a trace, and Katarina had no information to give on the matter. She merely said, _"I do not know,_ mi amor _, but I will ask him when I see him next, and I'll let you know as soon as I do."_

Dean had grumbled an _all right_ and went about his life, the funds from his rendezvous with the enigmatic Castiel rapidly dwindling with each red-stamped bill he received.

_”DEAN! Come ON!"_

Dean ran a hand through his hair and sighed, then unbuttoned the top button of his nicest shirt, which still had a rip in the hem that he could thankfully cover up by tucking his shirttails in, atop the pair of khakis that he had to wear with his work uniform.

He'd have to look up how to tie a tie the next time he went to the library.

That was to say, if he could ever manage to find _time_ to go to the library.

But for now, he had to go meet with his case worker.

***

Dean couldn't believe how far this situation had escalated. He was twenty years old, and his brother was fourteen. He made enough money to keep a roof over their heads and food in their mouths. He made sure Sammy got safely to school every day and then safely back home.

He didn't understand why the state wanted to take Sam away from him.

Sam was the only family— hell, the only _friend_ — he had left.

Now the state wanted to give him a lawyer. A goddamn _lawyer_ because everyone managed to have power in this situation but Dean. He'd completely lost control of the wheel somewhere down the line. The state was at the helm, fighting against itself, and all Dean could do was sit on the sidelines and watch.

Hopefully this lawyer dude would at least _listen_ to the voice of reason and not just give up on Dean like everyone else seemed to.

Naomi was nice at least. Sam liked her, and that was what mattered.

"How are you boys doing this afternoon?" she asked, crossing her hands over a mound of paperwork on her desk.

They were at the municipal building in a small office with a window air conditioner that rattled while it ran, and Dean and Sam were each sitting in folding chairs across from Naomi's small desk, the plate on the front of which read, _"Naomi Garrison, MSW."_

Dean had no idea what the 'MSW' stood for, so he added it to the list of things he needed to look up the next time he went to the library, because he was too embarrassed to ask.

"Great," Sam beamed, all dimples and mirth and perfectly straight teeth, because thank goodness John Winchester managed to pay the entirety of Sam's orthodontist bill before he passed.

God bless Sam Winchester, who was full of genuine happiness and affection for everyone he met, like a naive little puppy dog.

Dean loved that about his brother, and all he wanted to do was shield him from the world so that he would never, ever change.

"I got my report card," Sam continued. "I got all As again."

Naomi smiled and made a note on a form. "Well congratulations, Sam, that's wonderful to hear."

Dean didn't like talking in these meetings, even though Naomi was supposedly on his side. He felt like he always said the wrong thing, so, like when his father used to get mad at him, he kept silent, because silence wasn't nearly as incriminating as words were.

"And how have you been, Dean?" she asked, turning her attention to him.

"Good," Dean replied, terse.

She made a note on her form, and Dean straightened his back to look at the paper, but couldn't see what she wrote.

He wished he could get away with not saying anything at all.

"I called you in today to introduce you to your lawyer, so if you're both ready, we can take a little field trip to his office, sound good?"

Dean didn't know why she insisted on talking to them like they were children. Sam was still technically a child, yes, but Dean definitely wasn't, given that one of his occupations was now _prostitute_ and he had recently _taken it up the ass._

And he _liked it._

As Naomi guided them through the labyrinth of offices and cubicles of the municipal building, it reminded Dean of the stories Cas had told him about his own job as a lawyer.

Dean wondered what it was like having a job where he could sit down, where he would be paid to think instead of do what he was told, where he could make decisions and not worry about money.

He was pulled out of his reverie when Naomi lightly knocked on the door in front of them, and Dean was only able to catch the last three letters of _-vak_ on the plaque by the door before a set of familiar blue eyes caught his attention.

Cas's eyes only widened for a moment when he saw Dean before being replaced by the stoic mask he always wore, except, Dean noted, during an orgasm.

That face flashed across his mind, the way he looked two weeks ago when he was coming in Dean's ass, and his dick twitched at the thought while a flush crept up his face.

He looked away as Cas stepped aside. "Come in and have a seat."

That voice really didn't help matters in terms of what was going on in his pants. The moment he had caught Cas's icy gaze, he hoped that maybe the voice he reserved for the bedroom was somehow different than the one he used at work.

He was very, very wrong.

Cas's professional voice was just as rough and deep as the one that whispered filthy things into Dean's ear while managing to get him hard with nothing but a feather.

Dean put his hands in his pockets and shifted his dick, half-hard, so that it sat comfortably in his pant leg. 

Cas circled around his desk and, before taking a seat, held out his hand for Sam to shake.  

Sam took it while Naomi said, "Sam and Dean, this is the lawyer who will be working on your case, Castiel Novak. Mr. Novak, this is Sam and Dean Winchester."

Cas shook Dean's hand too, and their eyes met again.

Dean couldn't remember how to breathe as he shook Cas's hand, and he was sure his stunned face was giving him away, but Cas was the picture of cool, like he wasn't thinking about Dean's legs wrapped around his waist as he fucked into his ass.

It was all so fucking _weird_.

Cas retracted his hand and took a seat behind his desk, then opened the file folder Naomi had handed him.

The three of them took a seat in the chairs across from Cas's desk as he reviewed the paperwork.

After a moment, Cas said to Naomi, "I have a few more papers for Dean to fill out. Did you have anything you needed to work on with Sam this afternoon?"

Naomi smiled and replied, "Yes, actually. Dean can go ahead and fill out the forms while I finish up my session with Sam."

Cas looked up from the papers and smiled at her in return, but it didn't reach his eyes as he said, "That sounds great."

Dean had no idea how adults could stand speaking to one another like they were computers. Sure, Dean had to put on a fake smile for customers all the time, but that was different. He wasn't having full conversations with another person while sounding like a goddamn calculator. It was all just, _"Large combo or medium?"_ and, _"Have a great day."_

As much as Dean thought it might be cool to wear suits and be able to feel his feet at the end of any given day, it wouldn't be worth it if he had to be a cardboard cutout of a human being forty hours a week.

Before Sam left, he said, "It was nice meeting you, Mr. Novak," with a little wave.

"You too, Sam," Cas replied, and they walked out of the office, closing the door behind them.

Dean was alone with Cas.

The dude who _paid money to take Dean's virginity._

And now they were in his office.

Alone.

Right now was one of those moments where, if Sam were in his head, he'd say something like, _"You're getting real life confused with porn again, Dean."_

Dean didn't know when his life changed into a porn, but he'd be damned if he wasn't thrilled by this turn of events.

***

What the fuck was Cas's life anymore.

His goddamn _twink_ was sitting right in front of him, light blue dress shirt a size too small for him, which conformed to his body in a truly _sinful_ way, atop a pair of worn khakis.

And the fucking _look_ on Dean's face was  _destroying_  him.

Dean's perfectly freckled features were flushed pink, which of course forced memories into Cas's head that he couldn't let himself think about while he was _at work_ for godsakes _._

It didn't help that Cas's heart fluttered pitifully in his chest at the sight of Dean, looking so flustered by Cas's presence and so protective of his younger brother, like his mind was at war between the fact that Cas had taken his virginity not two weeks ago and now he was sitting in front of the poor boy trying to help him keep his brother in his life.

From a professional standpoint, Cas should have dropped the case due to a conflict of interest.

But then he'd have to explain, on paper, what that conflict was, and he couldn't let his employer, the state fucking government, know that he purchased sex from young men on a fairly frequent basis.

More importantly, Dean's case was actually very complicated, and Cas didn't trust anyone else with handling it. Cas _knew_ Dean. He'd seen the determination behind his fierce eyes, the intellect in them. He understood Dean to be, more than anything, adaptable, a survivalist, willing to do whatever it took to stay afloat.

No one else would look twice at the naive-looking high school dropout with the minimum wage paycheck who scowled more often than he smiled and only spoke when he was spoken to. No one else would give Dean a second thought, and Sam would immediately get taken away from him.

Cas sighed at the large file folder in front of him, and decided to take the morally ambiguous route: he'd take Dean's case, despite their previous tryst, despite his... _feelings_ for the boy, and he'd have to sever whatever it was that happened between them two weeks ago.

It was more important to Cas that he work to help Dean keep his younger brother in his life than upholding a fleeting romantic notion, which he'd been trying to dismiss for the past two weeks.

Without meeting Dean's gaze, Cas handed Dean a clipboard with a pen at the top and a stack of forms on top. "You'll need to fill these out."

As Dean took the clipboard from his hands, he replied, "Yes, Master."

Cas's head shot up, eyes wide. "Dean, that's inappropriate right now."

Dean met his glare and gave him a crooked smile, staring at Cas through a fan of long, dark lashes, and Cas almost broke the pen in his hand from what that look fucking  _did_ to him.

"Needed to figure out a way to get you to look at me." Dean's pretty pink tongue darted out to lick his perfect, plush lips, and Cas was immediately brought back to the way his divine features looked with Cas's cock shoved in that filthy mouth.

Cas looked at him, eyebrows raised and head tilted.

His apparent irritation didn't faze Dean. "What? Just because we're not in the scene doesn't mean we can't acknowledge... you know, anything?"

Cas pinched the bridge of his nose. "It's not that. It's just..."

He couldn't finish that sentence, because he wasn't thinking with his brain anymore.

"It's just what?"

Cas took a deep breath and met Dean's eyes again. "This is a... unique situation, and I'm not sure how to handle it quite yet, so if you could, please fill out those forms and I'll escort you back to Naomi's office."

With an indignant huff, Dean pulled the pen out of the top of the clipboard and read the first question of the form.

Cas stared again at the file in front of him, not reading any of the words, because his prostitute was now his client and their world was suddenly upside down.

He turned his attention to his computer to answer his newest email, when he heard shifting from Dean's direction.

Cas ignored it, because he had work to do and also because every time he looked at Dean, all he could think about was bending him over his desk and fucking into that pretty little ass of his.

When Dean entered his peripheral vision by standing and circling around Cas's desk to perch on the edge of it, Cas clenched his jaw and forced himself to continue ignoring the bratty little twink vying for his attention.

And when Dean leaned down to trail to trail up the inseam of Cas's pants while pressing a light kiss behind his ear, Cas clenched his jaw and said, _"Dean._ This is—"

Cas tried to finish his thought. He really did. But Dean cupped his erection in his palm and the entire world happened to have melted away.

"Inappropriate?" Dean whispered, lips grazing the shell of Cas's ear. "Wrong?" His tongue licked a light stripe up Cas's neck, hot and wet, and Cas had to let go of the mouse in his hand for fear of crushing it in his grip. _"Dirty?"_

Dean massaged Cas's dick, now rock hard, while pressing searing hot kisses up and down Cas's neck.

"What's the matter? Am I interrupting something?" He bit down lightly, then, dragging his lower lip across Cas's skin, whispered, "...Master?"

Cas had no idea how a sexually inexperienced twenty year old could utterly fucking _shred_ Cas's carefully constructed resolve time and time again, but he had no goddamn willpower around the boy and that was going to be a _problem._

He pushed himself away from his desk and grabbed Dean by the shirt to pull him into a fierce kiss.

Dean was as hot and sloppy as always and _fuck_ if it wasn't thrilling knowing that the small window in his door made them open to the fucking world. Anyone could see them or catch them but Cas's body was on fire and he'd lost complete control of himself.

He turned his chair and pulled Dean down on his knees between Cas's legs, then threaded his fingers in the boy's hair and yanked it backward.

Grazing his eyes down the long line of Dean's neck, staring into his defiant, manic glare, Cas growled, "You think you can come into my work and _seduce me_?" Then he kissed Dean again, deep and dirty.

Cas heard the sound of heels clacking outside his door, and it pulled him out of the scene, out of his trance, shoving the chair away from Dean's kneeling form as he tried to compose himself. "I'm sorry, Dean. We can't do this right now. The rules aren't the same here."

Dean pulled the chair back toward him by the armrests and smiled. "Sure they are. My safeword's the same. You'll keep an ear out for people walking by, and no one will be able to see me behind your desk." He reached up and pulled at the buckle of Cas's belt, staring up at him through those impossibly long lashes, lips slick and pink and just begging for Cas's cock to slide between them.

Voice rougher and huskier than normal, Cas said, "But we haven't agreed on price. Katarina normally handles that. It wouldn't be fair..."

Dean popped the button of Cas's pants and slowly slid down the zipper. "This one's on the house."

As he thumbed the fabric of Cas's boxers over his cock, Cas let out a broken, _"Fuck,_ Dean..."

Dean pulled Cas's dick out completely, and ran his hand up and down it, fingers gentle and slender against Cas's thickness.

Cas was really going to let this happen.

Half of him thought that he ought to stop this, tell Dean to get up and figure out how to get the state to find them another lawyer, because there was no way in hell Cas would be able to survive this.

The other half of him wanted to shove his cock so far down Dean's throat that tears came out of his eyes.

When Dean snaked his little pink tongue out of his lips to gently lick the head of Cas's cock, the latter won out.

"Get under my desk," Cas growled, and Dean let go momentarily to crawl the couple feet over so that he was safely hidden under the large desk.

Lithe hands ran up the length of Cas's legs and settled on his hips as Cas watched that perfect mouth wrap around the head of his leaking cock.

He felt Dean's tongue flick at his slit and impulsively ran his hand through Dean's hair, gripping it and pulling slightly, forcing himself not to buck into his mouth.

Knowing that Dean _wanted_ this made the whole thing so much better. The fact that Dean begged for Cas's cock, wanted to suck him down while they were _in public_ made Cas want to come right then and there, straight down Dean's little throat, and now Cas was staring underneath his desk as Dean sucked him down as far as he could go, which was only two-thirds of the way before Cas hit the back of his throat.

In what little light made it under the desk, Cas could see how pink Dean's cheeks were, exposing more of the innocent freckles that dusted his face. He pulled up a hand to grasp the remaining amount of Cas's length that wouldn't fit in his mouth, and _fuck_ this was too much to handle. Cas was in his goddamn _thirties_. There was no way he was already this close to coming.

Dean bobbed his head up and down, and Cas couldn't fucking help it when he bucked his hips little by little, fist in Dean's hair as he shoved just a bit further down Dean's throat, waiting until he swallowed around him, and _oh holy hell_ that felt amazing.

Cas lost his train of thought when someone knocked at the door. A face popped into the narrow window, smiling evilly in the way she always did, because she was his boss and because she was a sadist, too.

Of course Abaddon decided to stop in as his twink to whom he had too many emotional attachments was blowing him under his fucking desk. Of  _course_.

And of _course_ she entered without being prompted.

Cas pulled at Dean's hair to signal for him to stop, but Dean shook his head and continued.

_Fuck it all to hell._

Abaddon was all business, a nose-to-the-grindstone kind of boss, so she barely looked at Cas before thumbing through the files in her arms and dumping them unceremoniously onto his desk. "Here are the Fitzgerald files. His case is being transferred to you."

Dean started pulling off of Cas with each stroke, pumping all the way up and down his length and twisting slightly at the head with his fist, and it took all of Cas's mental faculties to reply, "Ohh," in conjunction with the moan that involuntarily escaped his lips.

She finally noticed that Cas probably looked like a damn trainwreck. "You feeling okay, Novak?"

Cas tried to look casual, so he propped his elbow on his desk hoping that his hips would dip away from Dean's mouth instead of further into it, but Dean would have none of it, and continued fucking onto Cas's cock with abandon.

Cas's voice was an octave higher than normal when he smiled, which was really more of a grimace, and said, "Never better."

Abaddon furrowed her brow and replied, "Okay, well, you need to get rid of that vacation time at some point, so if you're sick, just go home."

Cas gave her a thumbs up, completely disregarding the fact no one ever gave anyone else a thumbs up _except_ when they were trying to hide things like filthy little brats under their desk pumping furiously at their cocks like their lives fucking _depended_ on it. "Will do, boss."

Furthermore, he never referred to Abaddon as "boss," or anything, really, other than "heinous bitch" after he ended every call with her.

Dean lifted off of Cas's cock and blew on it. The sudden rush of cool air made Cas jerk forward.

One of Abaddon's eyebrows shot up, and she asked, "Aren't you supposed to have an appointment with the Winchesters right now?"

Cas's breath caught in his throat when Dean swallowed him down again.

For a boy who'd never sucked a dick until two weeks ago, he definitely caught on fast, because Cas was about five seconds away from coming in front of his own fucking _boss._

Cas cleared his throat, and tried to keep his voice even as he replied, "Yes. Sam is with..." Dean swirled his tongue around the head of his cock, and Cas's eyes involuntarily fluttered closed for a brief second while he bit his cheek to keep from groaning. He swallowed, forced his eyes open, and continued, "Naomi."

"And the older brother?"

 _Lie. Lie. Think of a lie. Fuck fuck_ fuck.

"Restroom," he croaked out.

His hands were gripping the edge of his desk so tightly that his knuckles were white and his nails left notches in the wood.

Abaddon nodded, and concluded, "All right, well when you're done, I think you should probably take a half day, okay?"

Cas steeled his jaw. "You're right. I'm not feeling too hot. I'll think about it."

"Good. Let me know when you're done looking at the Fitzgerald files and we'll touch base again closer to the end of the week."

Cas nodded in response, unable to breathe for fear of letting out an obscene noise, and Abaddon blessedly left the room, closing the door behind her.

He fell back onto his chair and looked down at Dean, who was still fervently sucking on his massive dick.

"You're such a filthy fucking _slut_ ," Cas grumbled.

Dean lifted off his cock for a second to reply, breathless, "But I'm _your_ filthy fucking slut, Master."

As he said that, Cas noticed that Dean had his own dick out, pumping furiously in time with his strokes on Cas's cock, and _god_ it was so fucking _hot_ that Cas wanted to come all over his face right then.

 _"Fuck_ , Dean." Cas gripped his hair again and thrust shallowly into his mouth, careful not to press too far, but it would just be so fucking _easy_ to fuck into his throat and stretch that pretty little mouth wide.

Dean popped off again to look into Cas's eyes and ask, appearing and sounding completely fucking _wrecked_ , "May I come now?"

Cas _wanted_ Dean to come, but he couldn't let him, not right away, not after Dean had broken so many rules and was just being a filthy, needy little twat about the whole thing, so Cas replied, "Only after I do."

He whined a little and nodded, then set back to work, swallowing the length of Cas's cock into his mouth again, immediately shoving himself as far down as he could go so that he could swallow around him repeatedly, only coming up for gasps of air when he needed to.

And _fuck_ Cas was so close already, but he wanted this to last longer, wanted to feel Dean's hot boyish mouth on him for just a few more moments because this would surely be their last time doing this, because he couldn't keep fucking his client. It was wrong on so many levels and he just—

A familiar fire built up at the base of his spine and every thought in his mind disappeared except for the heat enveloping his cock and the sinfully long lashes brushing over a cascade of freckles and broken little moans escaping Dean's throat. It was all too much to handle, so Cas held Dean's head steady in his hands and thrust up into his throat, coming down it with a sharp gasp as he felt Dean swallow it all down.

As Cas rode out the rest of his orgasm with shudders of his hips, the vibration of Dean moaning forced another wave over him. The filthy muffled noises of Dean fucking into his own fist with Cas's dick in his mouth was just about the _hottest_ thing Cas had ever encountered in his entire goddamn _life,_ and it pulled yet another pulse of pleasure out of him until he collapsed back on the chair, breathless.

Dean lifted off his dick and grinned up at Cas, cum trailing down his chin.

Cas reached over his desk and got some tissues for them to clean up, so Dean did, and zipped himself up before crawling out from under the desk and standing, stretching his arms above his head so that Cas could see a peak of those perfect, sharp hipbones framing a chiseled lower abdomen.

Cas was so _fucked._

Dean stuffed his frayed shirttails back into his pants, then circled around the desk to sit back down, and, looking at Cas like nothing had even happened, said, "So about my case..."


	6. Chapter 6

**Notes for the Chapter:**

> Please note I'm very sex worker positive. This isn't meant to be an educational piece on the sex trade. I'm not doing this for accuracy or anything, I'm just making it up as I go along. Nothing I write here is meant to reflect my perspectives on the sex industry.
> 
> That said, my sincerest apologies for putting this fic on the backburner for so long. This chapter is extra long and extra detailed in hopes that makes up for the hiatus. 
> 
> PS You might want to get your cold showers and/or bunks ready before you even begin. ;)

Dean never really understood what it meant to live paycheck-to-paycheck. He didn’t get that there was any other way to live.

That is, until the money started rolling in.

Still no word from Cas, but Katarina kept Dean busy. Now that he’d had a john under his belt—literally—the clients who were less fond of inexperience liked his look and ordered him as an entrée along with dessert.

Once Dean got the swing of things, he learned that turning tricks was a pretty fun gig. He almost had enough to pay off his father’s funeral and maybe get Sam new clothes for school.

There was Aaron, who was closer to his age and wanted to take him out on an honest-to-goodness _date_. He was a software engineer, some CEO of a major website Dean had never heard of because he rarely used the Internet. He liked vanilla sex in missionary only and, afterward, liked being the little spoon while he talked about his mom and sometimes cried.

There was this couple, Bela and Victor, who liked sandwiching Dean between them, while he fucked Bela and was fucked by Victor, and wow, _that_ was fun.

There was Pamela who was a little like Katarina but on the S&M side. Katarina had to give Dean an in-depth lesson on how to properly use slappers, paddles, and crops, but he was a quick study and Pamela left with a slew of deep red welts and a grin on her face.

Then there was Alastair, and he gave Dean the heebs _and_ the jeebs from the moment they met. That night hadn’t ended well, and it got to the point where Dean had to safeword out, but Alastair didn’t heed it. Thankfully, Katarina came in with some bouncers Dean had never noticed before and kicked Alastair to the curb. She gave Dean a thorough aftercare session and he felt better, but she also insisted that he take the week off and took Alastair off her roster for good.

After a week of only working sixty hours total at his other two jobs, Dean got bored. And horny. It didn’t help that Katarina texted him every few hours asking how he was doing, working under the assumption that Alastair had somehow traumatized him. It could have gotten ugly, sure, but she saved the day like always and it wasn’t too bad. The guy didn’t pull out when Dean freaked, but after some thorough talking-about-our-feelings stuff, followed by a rubdown, followed by unyielding praise, followed by cuddling, and now dozens of texts a day, Dean was ready to get back on the horse, so to speak.

Dean was watching _Dr. Sexy_ reruns with Sam while he worked on his homework, and he got a text from Katarina:

_How are you feeling? Is there anything I can do for you?_

The ‘mi amor’ was implied.

Dean sighed and ran a hand over his face. He knew what he wanted— _who_ he wanted—but for some reason, Cas stopped calling in. He really needed that emotional connection again that he hadn’t managed to feel with anyone else but Katarina, and right now Katarina was kind of overwhelming him with her concern.

After staring at his screen for several moments, hesitant, he replied:

_Has Cas requested me recently?_

Katarina replied immediately:

_I’m sorry. He hasn’t. If you would like to work tonight, you may come in and try to work the club._

The club was the basement of Katarina’s place, a bar of sorts that only served beer and wine. It was set up so that on Friday and Saturday nights, patrons could come in and hook up, either with one of the workers or someone just stopping in—everyone having required a specific invitation from Katarina herself, of course—then renting out one of the aptly-themed rooms and having a good time.

Dean had only been in there once while Katarina was giving him a tour, and had been hesitant about letting Dean work the club by himself until he got the hang of things.

Dean stared down at his phone, blinking. It was an incredibly high compliment to have been given this opportunity so soon. It felt like being promoted.

_Sure. I’ll be there._

***

Katarina’s club was different than any bar Dean had ever been to. The lighting was dim and red, and the music was quiet and unobtrusive. There were tables and couches and cushions everywhere, and it generally created an atmosphere of openness and acceptance.

Dean liked the club, feeling more relaxed after his first hour there than he had in the past week.

Katarina had given him the full run-down of how it worked when he arrived: it was his job to either sit at the bar looking lonely for someone to wander over and proposition him; or he had to walk around, mingling and seducing potential clients.

All of Katarina’s workers had to wear a rose pinned to their chest, so that everyone knew what was what and that money would need to be transacted.

Dean did what he felt most comfortable with, which was sitting at the bar, watching a game on TV and drinking a can of pop in hopes to allure any and all manner of tops or doms or bears or daddies to him—anyone looking for his type, really.

He wished there was a way _he_ could request Cas, but this gig didn’t work that way. He wasn’t allowed to pick and choose, and if Cas was out of commission, then there was no way he could contact him.

There was, actually, because he’d snagged one of _Mr. Novak’s_ business cards on his way out of the office. He could call Cas at work sometime, talk about the Sam situation together, but Cas made it very clear that there was nothing they could do beyond the case while it was being worked.

It hurt like a bitch, being dismissed like that, and while Cas was a great guy about it, and Dean understood why he had to do it, there was this tiny part of him that believed Cas was lying to him, and only saying that because he didn’t want to hurt Dean’s feelings with the truth: he didn’t like Dean, and he didn’t want to see him anymore.

Then, as if Dean had thought him into existence, the air next to him rustled as someone sat down next to him and said, “Hello, Dean.”

Dean looked over, wide-eyed, so shocked to see Cas that he wondered if someone had spiked his Coke.

“H-hey, Cas,” he stammered, taken utterly aback.

Cas looked tired, worn down, tie loose and suit looking even frumpier than usual. His five o’clock shadow looked more like a ten o’clock one, and he rubbed it with one hand while nodding slightly at the bartender to get his attention.

Instead of walking over, the bartender nodded in return and went to get Cas a beer.

Apparently, Cas was a regular here.

It shouldn't have surprised Dean, but a surge of jealousy roiled in his gut regardless. He didn’t like the thought of Cas scouting out other people, other workers, other _twinks_ without him knowing. He hadn’t been possessive of anyone else, but Cas was different. Cas was special.

The bartender came back with something amber-golden and foamy, sliding it over to Cas on a cocktail napkin. He thanked the bartender with a nod, and took a sip, then asked, without looking at Dean, “How have you been?”

Dean nodded, and replied, “Good. You?”

“I’ve been all right.”

So Dean may have been a little manipulative. He’d learned a lot from Katarina from working with her, watching her interact with people in the charming way she had, convincing everyone she spoke with that they were the only person in the whole world and that she loved them and cared for them with her entire being. It was heady, to be looked at the way Katarina looked at people. Everyone fell in love with her, and for damn good reason.

Pulling a classic Katarina tactic, Dean asked, “How is that… what was it that you were telling me about, the Chambers case? The one you were worried about?”

Not looking up from his beer, Cas smiled mirthlessly and huffed a laugh, shaking his head. “Not well.”

Dean shrugged, nonchalant, as though he’d have been just fine going back to scouting out clients bereft of legal conflicts of interest hanging over their heads, and continued, “What happened?”

Cas ran a hand through his already disheveled hair, and started talking, first about the court hearing and then about the home-visit. He went from refusing to make eye contact with Dean, to gesturing angrily, to shifting his body so that he was facing Dean on the barstool, their knees brushing together. He finished his beer and ordered another, and ordered another pop for Dean too.

Dean maintained eye contact, pretending he had horse-blinders on. He looked at Cas like Katarina looked at everyone: intensely, trying to memorize every word out of Cas’s mouth. He asked questions when he didn’t understand something, he nodded in sympathy, he never once used the word ‘I,’ and he listened, enrapt, to the whole story, which flowed into another, which flowed into another.

When Cas downed the last of his second beer, he stopped and sighed, looking at Dean and huffing another laugh. “I’m really sorry, Dean. You’re here to work and I’ve taken up all your time. I should get going.”

He got up to leave, but Dean caught his arm, and said, “Wait.” He was nervous about this next part, having mostly only been passive in his career as a sex worker, but continued, “If you want to talk more, we could go somewhere more… you know, private.”

He didn’t smile or cock his head to the side. He didn’t make it sound flirtatious. He wanted Cas to know that even if he didn’t get paid tonight, he wanted the man’s company. He wanted Cas to know that he was appreciated, even if no one else in the world did.

“Dean,” Cas began, “I don’t…”

Dean let go of his arm and shrugged. “It’s no big deal. I just thought I’d offer.” He looked around the room, which was dwindling rapidly as people either left or hooked up in private rooms, and added, “I’m not really feeling the crowd tonight anyway.”

Cas looked around too, apparently at war with himself, and nodded reluctantly, saying, “All right, lead the way.”

Katarina assigned all the workers at the club rooms and gave them keys along with the rose they had to wear. Dean had room number seven, and had never been inside it before, so when he unlocked the door and entered it, he was pleasantly surprised.

He knew that there were some rooms in this building that looked like sex dungeons, so he was thankful that room seven was more like a picture in a department store catalog. It was smaller than the penthouse suite, and the bed was full-size instead of king-size. The walls were a warm, dark brown and there were soft glowing track lights in the ceiling, casting a dim yellow around the room. The bed had an intricate wooden headboard and pristine white linens with lots of pillows.

It was modern yet elegant, not as sterile as a hotel but not as worn-in as a room in someone’s house. It was the perfect balance of sexy and cozy and welcoming, just like Katarina herself.

Cas walked in and took off his trench coat, then hung it up by a hook on the wall. His suit jacket followed, and he was left in his white shirt, rumpled and a size too big for him, like he’d lost weight recently. He uncuffed the buttons of his sleeves and rolled them up his forearms, then he toed off his shoes and socks.

Dean sat, perched on the edge of the bed, watching him. This time it felt different; there was less tension in the air, less apprehension. For a brief, blissful moment, watching Cas get comfortable, Dean could imagine that this was what it felt like to have a significant other, someone so close that it was okay to stare, it was okay to be attracted, it was okay to trust and feel the need to be trusted in turn.

He hadn’t known this was something that was missing in his life until this moment, this closeness not provided to him by Sammy, a level of intimacy that he hadn’t yet experienced, not with Lisa or Rhonda or even Katarina, who, for all her perfection, was still so layered that it was impossible to see what was beneath her carefully constructed façade.

But this was Cas, who was always so unapologetically himself, ugly suits and bags under his eyes and generosity flowing out of every pore in his body.

And Dean may have loved him a bit for that.

“Do you want to sit down?” he asked, propping his feet up on the bed and leaning against the mountain of pillows, patting the empty spot next to him.

Cas walked to the other side of the bed and collapsed down onto it, face first, planting himself in the pillows and groaning, “I hate my life, Dean.”

Dean laughed and reached out to rub consoling circles on Cas’s back, then jerked his hand away when remembered he wasn’t allowed.

Apparently Cas forgot too, because he groaned again and scooted closer to Dean.

 “Sorry, I thought…” Dean trailed off.

Cas lifted his head, and for a brief moment he looked confused, head tilted and eyes narrowed, before returning to his normal stoicism again. “You’re right. I forgot too.”

Cas rolled over and sat up, crossing his legs and clasping his hands together between them. He shrugged and sighed. “I apologize, Dean. I shouldn’t be unloading on you like this. You’re my cli—“

“Don’t you dare say ‘client,’” Dean interrupted.

Cas furrowed his brow and asked, “Why?”

Before Dean knew what he was saying, he blurted out, “Because, technically, you’re my client too. And more technically than that, you know that’s not what we are.”

He had no idea what he was expecting, but the blankness on Cas’s face told him that maybe whatever he said was a bad idea. He immediately retracted it. “Sorry, I didn’t mean that.”

Cas was still staring at him, stormy blue eyes focused and stern on Dean’s face. Dean couldn’t read what was behind them if someone paid him to, so instead, he felt like he was being interrogated somehow, like Cas was trying to pry information out of him against his will.

With another sigh, Cas shook his head and said, “I don’t think this is a good idea, Dean. There’s too much at stake here. My job, your brother.” Cas stood up from the bed to leave, but Dean leapt up and met him at the other side, stopping him with a hand in the center of his chest.

He was taller than Cas, only by a couple inches, but Cas was much broader than him, and even though his shirt was too big, his shoulders still managed to strain against it. Dean never thought of himself as attracted to men in a general sense, but Cas, right now, with the strong jaw covered in salt-and-pepper stubble, the intense blue eyes, the soft pink lips, the ripped body and lithe hands, made Dean rethink his previously stern position on heterosexuality.

Cas stopped and looked down at Dean’s hand on his chest before meeting his gaze. “Dean—“

“Stay,” Dean interrupted again. “Just… tonight. Then we can stop seeing each other except for meetings and court hearings and all that. I promise I won’t come onto you again.” He stepped into Cas’s personal space and leaned in, breathing the smell of clean soap and warm skin, and whispered, “Just one more time. I need this.” He lifted his hands and trailed them up Cas’s chest before concluding, “I need you.”

Cas shook his head, but didn’t step away. “Please understand that I can’t… I can’t believe you, Dean. Not when there’s money on the table.”

Dean stepped back and stared at Cas, aghast. “Wait. You think I only want you because of money?”

Cas gave him an exasperated look that said _of course_ Dean only wanted him for his money.

More than anything, Dean was hurt by that, to think Cas not only saw Dean as being low enough to show affection in the presence of cash alone, but to think of himself so lowly as to not believe he deserved Dean’s affections.

Dean was not a man of words where actions were better suited, so to prove Cas wrong, he leaned in and met their lips together in a long, hard, slow kiss that made Dean’s knees weak.

Cas was hesitant at first, and Dean thought he was going to pull away, but he let out a low breath that sounded more like a growl and kissed deeper, lifting his hands to cradle Dean’s neck between them.

After a long moment, Dean broke away, staring at Cas who stared back, wide-eyed and debauched. Dean reached up and unpinned the rose from his shirt, then tossed it on the small table by the door.

“Dean…” Cas began, staring at the rose for a moment before meeting Dean’s eyes. “You don’t have to do this. We _shouldn’t_ do this.”

Dean looked up at the ceiling and around the borders of it. Apparently the rooms in the club didn’t have the same level of security as the rest of the building. He looked back down at Cas and smirked, saying, “No one’s gonna know.”

Cas swallowed and Dean watched his Adam’s apple rise and fall. His entire body was tensed, as though he was physically restraining himself from touching Dean. After a deep breath, Cas said, “ _I_ would know. I need… I need to be the responsible one here, Dean. The adult.”

Dean threw his head back and laughed, _“You’re_ the responsible one? I’ve been raising my brother my whole damn life. I get three hours of sleep a night so I can keep him fed. I had to learn to change diapers when I was four, shoplift when I was ten, fix a carburetor when I was twelve, and started working full-time when I was fifteen years old. And now I’m sitting here telling you that you can fuck me senseless—for _free—_ because you’re the first goddamn person I’ve felt a connection with in as long as I can remember, and you’re telling me that you’re too fucking _moral_? Look, man, you either need to get off your high horse and fuck me, or get the fuck out and don’t come back.”

Cas stared at him in awe, slack-jawed, like he didn’t believe Dean was capable of speaking that many words consecutively.

Which, to be honest, Dean hadn't been sure he was either.

There was a tense pause between them, and the air was thick with apprehension. Dean didn't know why he said everything he just said, except he’d been through so fucking much this year already, and all he wanted was to be fucked and cared for by the man standing in front of him. He just wanted to appreciate Cas and show him as much without the dude assuming he was only in it for the money. He knew there was the whole legal battle going on, but what they did in private shouldn’t fucking matter anyway.

“I just—“ Dean began, but Cas interrupted by surging forward and kissing him with a level of ferocity Dean had yet to encounter in his life.

It was hot and fast and deep, and Dean felt like he was being devoured. Cas backed him up to the door and slammed him against it, trailing his lips down to mouth kisses on his neck. Dean leaned his head back, lips parted and eyes squeezed shut, groaning, _“Fuck_ yes.”

Between kisses, Cas mumbled, “You know I can’t deny you anything, Dean.” He reached up and began unbuttoning Dean’s shirt with one hand while the other groped his ass through his jeans. “Tell me what you want. I’ll give you anything.”

Dean rarely considered things in terms of what he wanted. He just knew he wanted Cas, any way Cas would take him. “I don’t know,” he replied, breathless, Cas’s mouth still on his neck and his fingers flicking open the last button of Dean’s shirt. “Something new. Something I haven’t done yet.”

Cas huffed a laugh against his throat, breath hot and sultry while teeth nipped at his skin. “Everything is new to you, Dean.”

Dean smiled at that, at the thought there was so much more out there to learn and experience. It was as heady as it was overwhelming. “Then do what you want with me. I’m yours.”

Cas broke away and took a step back, sitting down on the bed and leaning back on his palms. His expression was open and devious, the extreme opposite of what it had been just moments ago.

“Get undressed,” he said, quiet and forceful, that deep strength reverberating in his tone that was easy to ignore in the light of day, but shone like a beacon when the lights went out.

Dean smiled in return and leaned down to take off his shoes and socks and toss them by the door, then he stood back up and pulled his over-shirt off his arms.

“Slow,” Cas instructed, and Dean paused.

He’d done all manner of depraved shit recently, but somehow this, this simple act of undressing under the scrutiny of someone else, was different.

Dean had to close his eyes for this, feeling the blush creep up his chest and into his cheeks, then lifted the hem of his white cotton undershirt, dragging his nails across his abs. He bit his bottom lip and pulled the shirt slowly over his head, then threw it to the side, lowering his hands back down to pause at his nipples and flick them with his thumbs, lolling his head back. He reached down and popped open the button of his jeans, sliding the zipper down, and reaching into them to grab his dick, so hard it throbbed and jumped at his touch.

He ran a loose fist over it a few times, still rubbing his nipple between his finger, beginning to breathe heavy as the world melted around him. He could feel Cas’s eyes on him, and he opened his own to see the man drinking him in greedily, face flushed and chest heaving. His hands were twisted in the sheets, white knuckled as he watched.

Dean pushed down the fabric of his boxers to the base of his dick, relishing in the breeze of the room over his heated prick. He continued pumping himself languidly in his own fist, reaching down with his other hand to cradle his balls as he kept his eyes trained on Cas, who looked increasingly wrecked as the moments dragged on.

When he started to feel the heat well up in his stomach, he let go of himself to hook two thumbs in the waistband of his pants and slowly push them down, writhing out of them and kicking them to the side.

He stood back up and Cas whispered, voice strained and impossibly deep, “Come here.”

Dean stepped toward the bed and climbed on top of it, one knee on either side of Cas’s hips, sitting on his thighs and bending down to kiss him.

Cas’s soft hands ran up and down his back, gripped his hips and pulled him closer so that Dean could feel Cas’s dick strain against his pants. A pearl of cum leaked out of the tip of Dean’s cock and rolled down onto the fabric of Cas’s fly.

Cas kissed his neck and chest, trailed more kisses downward until finding a nipple and laving at it, pulling it between his teeth and gently sucking on it. Dean groaned and threaded his fingers in Cas’s hair, impulsively thrusting against Cas’s clothed dick and loving the feel of his wetness staining it.

Wrapping his arms around Dean’s back, Cas gripped him tight and lifted him up to turn them around and set him back down on the bed. Cas knelt between Dean’s spread legs, and in an instant, they were kissing again, desperate and messy, panting as Cas grinded their hips together.

He reached down and took one of Dean’s wrists, brought it over his head and pinned it there, then found the other and did the same, both of his hands in Cas’s tight grip.

Dean groaned at that, at the feeling of being restrained, and bucked his hips up again.

Cas leaned down and whispered, “You like that? You like being at my mercy?” He trailed his free hand down Dean's side and traced his fingers lightly over his hipbones.

Dean nodded, lip bitten between his teeth.

“Good,” Cas said, pleased, then wrapped his hand around Dean’s cock and fisted it slowly, slicking the steady stream of fluid around the shaft and twisting upward at the top.

The pace was too slow for Dean to come, but too fast for him to ignore, exactly at the spot where Dean had to close his eyes and whimper, writhing, half shoving his hips harder into Cas's fist and half tempted to beg for more.

The most infuriating thing was that Cas was still completely clothed, eyes open and watching Dean as he took him apart, leaning down on occasion to lick or kiss or bite or tease a nipple, never relinquishing the hold on his wrists.

“Please, Cas,” Dean pleaded, voice cracking. “Please fuck me.”

Cas leaned down while thumbing at Dean’s slit, earning him a shocked gasp, and asked, “May I tie you up?”

Dean’s eyes shot open and his breath caught in his throat. He could only manage a slow nod in response before Cas was off of him and walking over to the dresser by the bed.

He pulled out two items from the top drawer, then closed it, opened the second drawer, and pulled out two long strips of black silk fabric.

When he stepped back toward the bed, he tossed the items down, and Dean hoped he would take off his clothes. Instead, he climbed between Dean’s legs and leaned down to kiss him once before peppering the center of his body with kisses, down further until stopping at his navel. He licked a stripe up Dean’s hipbones and then mouthed at the shaft of Dean’s cock, which was so sensitive that it made Dean gasp out a high-pitched whine.

Cas huffed a small laugh against it and licked up the length of it, stopping at the tip to drag his tongue around the head and suck it in his mouth.

 _“Fuck,”_ Dean groaned, using all his effort not to fuck into Cas’s face.

He lost the battle and shifted his hips upward, so Cas reached an arm around and steadied his hips while taking his entire length in his mouth.

Dean cried out, barely able to withstand the blissful heat of Cas’s lithe tongue against the bottom of his dick, swirling around while his head bobbed up and down. He reached down and threaded his fingers through Cas’s hair, pulling slightly to keep from pushing Cas’s face down onto him further.

Dean’s breathing became ragged, hitched breaths escaping his lips faster and faster, body tensing up, fire at the base of his spine building. He could barely form words, but he managed a, “Cas… I’m…” while thrusting his hips against Cas’s strong arm across his waist.

Cas looked up at him, bright blue eyes challenging Dean to go ahead and do it, spill his load down Cas’s throat, pink lips reddened and swollen and stretched around Dean’s cock, taking him all the way in.

That was all it took for Dean to come with a shout, twisting Cas’s hair in his fingers and feeling his own cum mix against his dick with saliva until Cas swallowed it all, the reflex of his throat catching around the head of Dean’s cock as Dean rode his orgasm down.

When Dean began twitching with oversensitivity, Cas pulled off and immediately crawled up Dean’s body to kiss him, groaning into his mouth. Dean could taste himself on Cas and _fuck_ that was hot for all the wrong reasons.

Dean’s skin was on fire and he was still catching his breath, feeling warm and relaxed and sleepy, but Cas wasn’t done with him yet. “Turn over,” he instructed with another light kiss to Dean’s lips.

Dean rolled over onto his stomach and Cas straddled his ass, running his hands up and down his back, stopping at his shoulders to knead out the knots in them. Dean was pliant and relaxed, letting out muffled moans into the pillow. Then Cas wandered down lower and massaged his ass and the backs of his thighs.

When he was done with the massage and Dean felt like putty, Cas gently lifted at his hips and said, “On your knees.”

Slowly and weakly, Dean propped himself on his hands and knees, having no idea what Cas was going to do to him but wanting it anyway, just loving the feel of Cas’s hands on his body, of Cas looking at his body and taking him all in.

“I’m going to tie your wrists to your ankles. Is that all right?” Cas asked, voice filled with concern, apprehensive considering the paradigm shift of their situation.

Dean’s reply was rough and lazy. “Yes,” he said, unable to put in the intonation he wanted to, that despite how relaxed he was, he wanted everything Cas had to offer.

Cas took Dean’s left wrist and pulled it gently downward to rest beside his left ankle, then grabbed the silk scarf and tied it expertly around each, pulling tight and knotting them together. He put two fingers inside it and spun them to make sure it wasn’t too tight before moving over and doing the same with Dean’s other wrist and ankle.

“Is that okay?” Cas asked, running a soothing hand up and down Dean’s thigh. “Good?”

The position was… interesting. Dean’s face was planted in the pillow with his head turned, his neck, shoulders, and knees taking the brunt of his weight. His spine was contorted in a convexed angle so that his ass was angled high, legs spread open, completely exposed with nowhere to hide.

It was so fucking _hot_.

“Yeah,” Dean replied, muffled against the pillow, feeling his dick twitch with interest at the splayed open position alone. The air of the room felt cool against his ass, and despite the mild discomfort, he felt _sexy_ like this, all bound up and waiting.

As though Cas could read his thoughts, he rubbed his hands up and down Dean’s back again in reverence and said quietly, “You are so beautiful.”

Dean was thankful that Cas couldn’t see the blush that crept up his face.

Cas leaned in and blew lightly at his hole. Dean wanted to jump at the sensation, but his bounds kept him in place. It felt strange, and sent a shiver down his spine, set a whole horde of butterflies loose in his stomach.

Then Cas’s lips were kissing down his crack, open-mouthed and wet, and Dean was left with this intense need for Cas to lick him open, to feel that hot tongue on his hole.

Thankfully, he was just as impatient as Dean, because the next moment he was licking at his entrance, the tip of his tongue swirling around it. Dean was even more fucking thankful for being twenty years old, because he was already hard again, leaking steadily in response to the new sensation, pre-cum dribbling down his cock and onto his balls.

Cas slowly worked him open, getting him soaking wet and then darting inside, pulling out to lick around again. Eventually, he began fucking Dean’s hole with his tongue in earnest, the stubble of his jaw dragging against the sensitive skin of Dean’s ass.

The noises Dean made were embarrassing, breathy and high-pitched whining, pushing backward onto Cas’s face to get him to go deeper, to fuck him open wider. He nearly screamed when Cas reached up and slid one finger into his hole easily, continuing to lave around his entrance while pumping him with his finger, slowly and methodically.

“Another,” Dean rasped, beside himself with want.

Cas pulled his finger out and rubbed two against the slick wetness before pressing them in together to the knuckle, pulling back out, and pressing in further. He scissored Dean open while continuing to lick around his hole and up and down his crack. The sensation was so intense that Dean could barely breathe. He wanted to move, to writhe and buck and turn around to tackle Cas to the bed and sink down onto his cock, but all he could do was take it, ass propped high in the air and straining against the binds at his wrists and ankles.

 _Finally_ Cas added a third finger, and it burned in the most blissful way, Dean’s hole stretching open around him and wanting to take more. He gritted his teeth and closed his eyes against the pain which mixed so closely with pleasure that there was no difference anymore, especially when Cas bent his fingers and grazed over his prostate.

Dean shouted and thrust backward, wanting it again, and Cas gave it, pumping steadily into him and pressing against his sweet spot with each sweep of his fingers. Dean gasped and cried out and bit the pillow to keep from screaming. The feeling wasn’t enough to make him come again, so instead he just hung there at the precipice of utmost pleasure, completely at Cas’s mercy, being tortured in the absolute best of ways.

Cas pulled out and Dean felt horribly empty. His stomach sunk in disappointment until he heard a zipper being pulled down, then a wrapper being ripped open, the distinct sound of latex unrolling, and the cap of a lube bottle opening.

The lube was cold against his ass as Cas slid some onto him, sliding inside him with three fingers again, his hole slick and greedy and more ready for Cas’s cock than it’d ever been.

When Cas lined up with him, he slid his dick over Dean's hole, teasing it, flicking the head against it and away again. Dean could feel himself tense with every little tease, gasp every time Cas bumped into the edge of his rim with the blunt head of his cock.

 _"Please,"_ Dean begged, his voice barely above a muffled growl.

He could feel Cas smile behind him as at last he pressed in, his cockhead opening Dean wide as he slowly slid into him, an inch at a time. He bottomed out with a groan and bent over Dean’s back. Dean could feel the cold leather of Cas’s belt across the backs of his thighs, the cotton of his shirt on his ass.

The fucker was still _dressed_. Dean could picture it, picture the both of them: one of them hogtied, face down, ass up, begging to be fucked; the other clothed in goddamn business attire but for his cock freed and sheathed in Dean’s ass.

“Move,” Dean mumbled in desperation, pushing back against Cas with what little ability of movement he had.

Cas moaned and sank into him again, over and over, angling his hips in such a way that he was nailing Dean’s prostate with every thrust.

It felt so damn good that Dean’s vision blurred at the edges. His jaw hung loose and every breath he took was a whimper or a moan or Cas’s name, like a prayer escaping his lips. The wet slapping sound of being fucked into was music to his ears. The feel of the scarves tied tight around his wrists was the kind of grounding force he’d always needed and never understood before; the ability to be bound by someone and open to them to do with what they pleased. Dean never wanted this feeling to end.

Cas fucked faster and harder and eventually lost his rhythm, hips stuttering erratically, thrusts becoming more shallow until he was only grinding in circles against Dean, buried to the hilt and still trying to go in deeper. His hands were sweaty and gripping Dean’s ass hard enough that it hurt, but he let go to reach forward with one hand and card his fingers through Dean’s hair briefly before gripping it in his fist and pulling his head back.

“Oh _fuck,”_ Dean exclaimed as Cas pounded into him, and his second orgasm suddenly ripped through his body, hot white stripes coating the sheets underneath him and dripping down his cock and balls and legs. Spurts landed on his chest and chin and he came for so long, he thought it would never stop.

Cas continued fucking into him, breathing harsh, until Dean clenched around him one last time on an inward thrust, and Cas let go, coming with a cry, hips stilled as he filled Dean completely. Dean could feel his hard cock shudder and convulse inside of him, and it was the best thing he’d ever felt in his whole goddamn life.

Cas gripped the base of his cock and pulled out gently with a strangled sigh. Before he did anything else, he untied the scarves and rolled Dean over on his back, massaging and kissing the deep red welts on his wrists and ankles. “Are you okay?” he asked, meeting Dean’s fuzzy gaze. “Are you numb anywhere? Are you in any pain?”

Dean couldn’t find the words to reply, so he gave a short shake of his head. Cas lifted his wrist to his mouth and kissed it once more before getting up from the bed and removing the condom, tying it off and tossing it in a trash can, then wetting a towel in the bathroom and coming back to clean Dean up, a glass of water in hand.

He made Dean sit up and drink it while rubbing the warm cloth over his body, which made him hazy and sleepy. When Dean was done with the water, Cas took the glass away and set the cloth down, then pulled the covers out from under them and draped them across their bodies.

Cas held Dean in his arms and peppered the backs of his shoulders with kisses, murmuring, “You can sleep, Dean. I’ll make sure Katarina knows you’re safe.”

Dean nodded and dozed off with the feel of Cas’s strong body around him, the feel of Cas's nose and lips at the back of his neck, kissing him absently now and again.

Before he let the darkness consume him, Dean swore he heard Cas whisper, “I love you.”


	7. Chapter 7

**Notes for the Chapter:**

> It's been a while. Sorry about that. For your patience, I now give you a scene which required me to add twice as many tags and an archive warning, and which makes me incredibly nervous to post because of how far I stretch the boundaries of what I deem to be tasteful smut.
> 
> I'll be posting the next chapter soon so I can finish out this fic. 
> 
> B&E beta'd the first half of this chapter, so thank her for my lack of horrible grammatical errors in the beginning.

It was the week before the trial, and Dean could barely sleep, or eat, or do anything other than bite his nails and tick off the items on his endless to-do list. He needed to run to the bank, go to the laundromat, do the grocery shopping, and mail out some bills, all between his morning shift at McD’s, his afternoon shift at the shop, and his evening shift at Katarina’s with his new dom, Benny.

Benny was a bear who was also a blast and a half, the kind of guy Dean wouldn’t mind watching the game with after being fucked senseless. He was some kind of BDSM minimalist: no toys, no games; no aftercare; no promise of punishments or rewards. He gave orders, and Dean followed them. Dean had been curious from the moment they met what would happen if he blatantly defied him, but he also had no desire to follow through with it.

Benny was the kind of dom who demanded respect and gave it to his subs in turn. Dean was obsessive about receiving praise from everyone else, but with Benny, he could do no wrong, and that was what made it fantastic. He had Benny’s unyielding acceptance as long as Benny had his unyielding obedience in return.

It was balanced, and it worked. And best of all, it was _fun._

Dean hadn’t heard from Cas in weeks, not since a clipped phone conversation relating to his case that was overly-professional and cold. Dean tried flirting his way through it, hinting in the way Katarina taught him that he’d like to see Cas again, in any way, shape, or form, without seeming desperate for it.

But he _was_ desperate for it. He missed their chemistry, the electricity between them. He missed how well they seemed to communicate without needing any words at all. He missed listening to Cas rant about his job, the way he looked at Dean with open curiosity when Dean talked about his own life.

Most of all, he missed being touched by Castiel. No one else could touch him the way Cas did, not even Katarina. It was commanding and possessive and _loving_. It calmed Dean when nothing else could, and filled this horrible, gaping hole in his heart that he didn’t even know was there until Cas showed him Dean was worth a damn. There was just something different about Cas, and when Dean thought about it, his heart raced and his stomach flopped, and he could feel himself blush, even when he was elbow-deep in an engine.

Dean knew without a shadow of a doubt that Cas was busting his ass on Dean’s case, but he wasn’t sure if that was why Cas had been so distant. He _hoped_ that was the reason, and not because their relationship had turned into to some kind of gay, age-discrepant _Pretty Woman_ situation.

Benny kept his mind off things at least, and the dude was loaded enough to hire Dean every night he was available. He was some kind of contractor or franchisee or real estate investor, one of those guys whose income tax return was probably thicker than the Oxford English Dictionary. All Dean knew was that the dude had a lot of dough and a lot of time on his hands, and he was more than happy to help him with both of those problems.

When Dean’s shift was over at McD’s, he tossed his hat into the Impala to book it to the bank before his shift started at the shop, and he felt his phone vibrate in his pocket.

While he shoved his keys into the ignition, he read it. It was from Katarina:

_Would you be interested in doing a show this weekend?_

As part of Dean’s training, Katarina let him sit in on a “show,” which was basically a raised platform whereon something sexual happened, and many people wearing masks paid to watch.

Dean watched Meg and Ruby go at it, and at the time, he was pretty sure it had been the highlight of his life. It took every ounce of willpower not to squeeze one out while he watched, but Katarina praised him for his resolve, ran her fingers through Dean’s hair and cooed at him about being a _good boy_ , which was about a billion times better than coming in his pants like a teenager.

Before putting the car into gear, he typed back:

_Details?_

The bank was only a block away, and by the time he got there, Katarina hadn’t yet responded, which wasn’t like her.

He was waiting in the teller line when she finally did, and Dean almost dropped his phone when he read the text.

_You and Anna together will be the first act. The second act involves being fucked by anyone who purchases a participation ticket, and there will also be spectators. I will be on stage with you the entire time, watching but not participating. The show will last approximately two hours and your payment will be $3,000._

“Holy shit,” Dean muttered as he was called up to the teller window. He pocketed his phone with trembling hands and greeted the cute blonde smiling at him, then asked to withdraw a comparatively measly four-hundred dollars to pay rent.

“I’m sorry, Mr. Winchester, that amount is unavailable,” she said with a forced frown.

“What?” Dean asked, leaning over the window to try to look at the monitor. “I should have like five-hundred in there.”

She printed off a paper and showed it to him, then pointed at several transactions that made Dean’s eyes bug out of his head. “It looks like you received ten overdraft fees this month.”

“You’ve gotta be fucking kidding me.”

After several more words which escalated in the security guard asking him to leave, Dean balled up the statement paper in his fist and stormed out of the bank, fuming and feeling like a total fucking failure. He pounded his head against the steering wheel a few times before smashing out a text back to Katarina:

_I’m in._

***

The “theater” was a big finished basement in Katarina’s brothel. It wasn’t quite a sex dungeon, but it also wasn’t as warm and inviting as all the other rooms. The cement brick walls were painted white; black fabric covered the small windows near the ceiling; the lighting was dimmed to tasteful sconces on the walls; and the platform was surrounded by black metal folding chairs.

About an hour before the show, Katarina prepped Dean and Anna on what was about to happen. While Dean had never worked with Anna, they’d spoken a few times, and she was exactly his type: shy and witty, big eyes and a wide smile. He was grateful that his instinct told him Katarina would disapprove of employee relationships, though, because at least that covered up the overwhelming feeling in his gut that he really only wanted Castiel anyway.

But Dean didn’t like thinking about that.

Katarina hadn’t dressed in her uniform yet, so she was clad in a pink tank-top and black yoga pants, and it did all sorts of things to Dean’s brain and pants. There was just something so much sexier about Katarina in plainclothes than Katarina in dom attire, like she was sharing some deep secret with Dean and Anna that she was actually a normal human being somewhere under all of her _mi amores_ and riding crops.

On of the platform sat a waist-high bench, and on top of it lay an assortment of items, and Katarina barely looked up from her phone as she led Dean and Anna to the middle of the stage. She put her phone in her sports bra and looked at them, face set completely to business.

“Tonight you will be fucking one another until both of you come. I will be giving you step-by-step instructions on stage as to your positioning. When you are done and the audience is warmed up, I will blindfold both of you and put each of you in these.” Katarina picked up a shiny metal spreader bar with attached cuffs. “All of the participants will be male this evening, and they will line up behind either of you depending on their sexual preference. They may either fuck you for five minutes or until they orgasm, whichever happens first. You of course may safeword at any time. Do you have any questions?”

Anna politely raised her hand. Katarina nodded at her with a warm smile and said, _“Mi amor_ , we are not in a scene. You may speak freely.”

“Oh,” Anna replied, a small blush on her perfect pale skin. “How many participants will there be, and how many audience members?”

Katarina pulled out her phone and clicked a few buttons. “Twenty-four participants, thirty spectators.”

Dean did some quick math. “So we have to fuck each other, and then be fucked by about a dozen dudes for five minutes each, while a bunch of other dudes watch?”

_“Si.”_

Not six months ago, Dean would have been horrified at the thought of being touched by another man, let alone being fucked by another man, let alone being blindfolded and fucked by a dozen men consecutively in front of an audience and then paid three grand for his efforts.

But a lot had changed in six months, so Dean replied with a grin, “Great, when do we get started?”

Katarina picked up a large black plug from the array of items on the bench, and, devious smile spreading across her face, said, “When you are finished prepping, _mi amor.”_

***

An hour later, Dean re-entered the theater clad in a fuzzy white bathrobe. Anna was already there, in a matching bathrobe, sitting on the bench and studying one of the spreader bars.

“Never used one of those?” Dean asked, sitting beside her on the bench. The plug pressed against his prostate and he stifled a gasp, but his breathing remained shallow, cock already twitching beneath his robe.

Without looking up at him, she replied, “Not yet. Most of my clients are pretty vanilla, actually. Katarina must think I have a type.”

As if on cue, Katarina’s stilettos clacked against the floor as she entered the theater in her usual work get-up.

Dean’s cock twitched again, and suddenly he was dying to get started. Katarina had made him go on break for a week and requested that he not touch himself in preparation for tonight, so that he could come as many times as necessary. There was this itch underneath his skin, this deep craving to be spread open and fucked into oblivion. The plug resting inside him did little to help matters, and his body was unconsciously, minutely writhing, shifting the plug in a small, rhythmic motion. He was warm all over, and he had to clench his hands into fists to keep from touching Anna. He needed to feel someone else’s skin after a week bereft of touching another person, not realizing until now the necessity he had developed for physical intimacy. Because he got paid for it, it brought a whole new meaning to the term ‘workaholic.’

“Good evening, _mi amores,”_ Katarina greeted in a sing-song voice. “Are you both ready?”

“Yes, ma’am,” Anna replied, eyes averted, at the same time Dean said, “Yes, Mistress.”

After a thorough warm-up—to Dean’s immense confusion, Katarina proceeded to work them through a mild yoga routine to stretch them out because, as she said, “You will be bent over that bench for a long time”—Dean and Anna sat next to each other in standard position: kneeling, gaze downward. Dean forced himself to stare at his hands and breathe deeply and steadily, which was increasingly difficult with each new pair of steps that entered the theater, knowing they could see him, naked and vulnerable, plug up his ass that relentlessly teased him despite sitting perfectly still.

Dean finally found his calm—what Katarina referred to as “subspace”—about ten minutes into the increasing flow of the arrival of the audience. His mind slowed to a blissful emptiness, trusting Katarina with his whole being to provide him thorough instruction when he was needed.

It was no longer necessary to have control of his body, because Katarina controlled it for him.

No one spoke. As people arrived, they took a seat, and all Dean could hear were periodic footsteps and the soft scraping of chairs on the hardwood floor. When the footsteps stopped, the platform vibrated with the stiletto clacking of Katarina’s boots as she circled around in front of them, the sharp slapping sound of a riding crop hitting the palm of her hand methodically as she walked.

“You all know the rules,” she began. “But I will remind you anyway. One, protection is a necessity. You will be provided a condom, and you will wear it. Two, no heckling, hitting, spitting, biting, or hair-pulling. Tonight is for show only. Three, participants are wearing red masks; spectators, black. No spectator may touch anyone but themselves. No participant may touch anyone other than a sub. Four, keep both noise and clothing removal to a minimum. Five, no cameras or recording devices are allowed in this room. Six and most importantly, if a sub safewords, you pull out and walk away _immediately_. Tonight’s safeword is ‘pineapple.’ If you fail any of these rules, you will be escorted off the premises and you will not be invited back.”

From Dean’s peripheral vision, he could see Katarina turn on her heel and face them, feel her gently run her fingers through his hair. “Time to stand, _mi amores_ ,” she whispered.

Dean stood, and looked out into the sea of audience members, all in normal clothes but for red and black masks. He felt exposed as a blush crept up his chest, and swallowed audibly.

Katarina took his chin and turned his face toward her. “Eyes on me or Anna, Dean. They are paying to watch you, not to watch you watch them.”

Dean nodded, and a thin pang of guilt ran through him at the thought that he already screwed this up, but Katarina thumbed over his cheek and whispered, “You are a good boy, Dean. Let your talents shine tonight, and you will do very well.”

Katarina spun him slowly by the shoulder to face Anna, who looked about as nervous as Dean felt, even though he was pretty sure she had already done a show or two before. It made him feel better to think that it took practice to get to the level of comfort that Meg and Ruby seemed to have when he watched them on stage.

“Anna, kiss Dean,” Katarina commanded as she circled around them.

Anna took a step forward, hair in a tight bun at the back of her head, pale and naked and beautiful. Dean tried to be a gentleman and keep eye contact only, to stand still as Anna perched on her tiptoes and lightly brushed her soft lips to his.

“Dean, you may touch Anna.”

Dean exhaled in relief and placed a tentative hand on Anna’s waist, pulled her closer as she deepened the kiss. Her breasts pressed against his ribcage, and Dean was thankful for all the months of practice he’d had at restraint, learning how to put his faith in the direction of another person. It taught him patience and calmness, and within minutes he was back in his subspace while Katarina guided them. The audience remained silent as if they fell away and all that was left were Dean and Anna, obedient subs following words that eventually flowed into them like they weren’t being spoken at all.

One moment, Dean and Anna were standing and kissing, and the next, Dean was straddling the bench with Anna on top of him, lowering herself onto his cock. The angle forced the plug to brush against his prostate, and Dean was already panting for breath, stomach muscles clenched in an effort not to scream. Anna was wet and tight and gasped quietly as she found a steady rhythm, head thrown back and eyes squeezed shut.

Katarina straddled the bench behind Dean and murmured quiet praises, reached around him to gently thumb at Anna’s clit while she pressed soft kisses to Dean’s shoulders. The praise went straight to his cock, the burning at the base of his spine growing slowly, and he pushed it back, forced it away until directed to do so. Her other hand trailed down his back, reached underneath him to take the base of his plug and circle it around. Dean cried out, and unconsciously thrust back onto to it. She laughed deviously into his shoulder and whispered, “Good boy.”

Katarina moved to stand behind Anna, peppering her neck with kisses and murmuring something Dean couldn’t hear. She reached around Anna and pinched a nipple between her thumb and forefinger, pulling it and teasing it slowly, smiling into Anna’s neck.

Anna gasped and fucked onto Dean faster and harder. Dean held her by her hips and met her thrust for thrust as quiet, breathless moans escaped his throat.

Katarina reached between them and circled Anna’s clit. Dean watched as she licked up the shell of Anna’s ear, bit gently on her earlobe. He could feel the slight brush of Katarina’s fingers on the base of his dick as Anna moved up and down on top of him.

Anna threaded her fingers through Dean’s hair and pulled him closer, their thrusts losing rhythm, growing shallow as they both fought back the orgasms threatening to rip through them.

Katarina moved to the side and faced the audience. Dean’s face was pressed against Anna’s chest as she ground on top of him, fast and hard, rubbing her own clit, moans growing louder between panted breaths.

“Please,” Anna begged. “Please, ma’am, may we come?”

It was a bold move, to beg during a show, but Dean had been on the precipice for so long that he thought his mind would unravel if he couldn’t come soon. His thighs trembled with the effort, cock so hard that it throbbed inside Anna, plug relentlessly brushing his sweet spot to the point that he couldn’t even hear the noises coming out of his own throat anymore.

 _“Please,”_ he heard himself say, cracked and broken with a hint of a whimper at the end.

Anna lowered her face to his neck as he continued thrusting into her, whining out, “Oh fuck, oh fuck,” over and over again. He could feel her shaking, body blushed over and fever-hot. Dean’s hands were sweaty where they’d been holding her hips so he dug his fingers in, pushed into her deeper, seeking any amount of relief.

Like a command from God Herself, Katarina finally said, “You may come.”

Dean didn’t know such a sound could come out of someone so small when Anna shrieked in pleasure. Her pussy pulsed against Dean’s cock rapidly, pushing Dean over the edge too until he came with a strangled cry, holding Anna still on top of him as the waves hit him with mind-blowing intensity.

Anna went limp against him as they both caught their breath. He held her and rubbed her back while she absently kissed his shoulder and neck and breathed out a quiet, “Wow.”

Katarina circled around in front of them and faced the audience. “We have now reached intermission. In ten minutes, we will resume with act two. Please prepare as necessary.”

***

As politely as possible, Cas shifted his cock more comfortably into his pantleg and straightened his black mask on his face absently, like he would with a pair of glasses and not a flimsy piece of nylon to hide his identity in midst of a brothel’s sex dungeon.

Watching Dean fuck Anna was a beautiful sight, and while Cas was more than happy as a passive voyeur, this is the first show he’d been to where he had to physically restrain himself from getting up and taking Dean as his own, like a fucking Neanderthal.

It was Castiel’s fault, really. He could have asked Katarina who was starring tonight. He could have upgraded his spectator ticket to a participant one. And moreover, he could have just left when he saw Dean Winchester— _his_ Dean, the young man who didn’t even know that he held Cas’s heart in the palm of his too-callused hand—knelt on the stage before him, all freckled, blushed skin and a familiar whole-body excited-nervous tremor.

Cas had done that to him once, what seemed like forever ago. Castiel used to make Dean shiver and pulse and writhe and moan. In a manner of speaking, he took Dean’s virginity.

Watching the way the audience watched Dean—dozens of large, predatory, faceless men--Cas felt the beginnings of hideous, ugly possession pulsing in the pit of his stomach.

He’d slept with so many of Katarina’s young subs, and he’d watched them all grow and change and find a different range of clientele when their newness wore off for him. He’d seen them in shows and enjoyed watching them use tricks and techniques that he’d taught them (that Katarina had probably taught him years prior, back in New Orleans).

But Dean was different.

Cas could have left. He _should_ have left as soon as Katarina called intermission. He only came to the show to blow off some steam, walk away from his desk that was piled with papers and files all titled in some way with “Winchester.” The boy was haunting him without even being in his life anymore.

Next week was the trial, and there Cas was, in a sex dungeon, watching wide-eyed and helpless as Katarina slowly pulled a large black plug out of his twink’s ass.

***

It might have been in Dean’s head, but the clicking of the lock around his wrists seemed to echo in the theater. Katarina ran a soft hand up his arm and whispered, “Are you sure you are ready for this?”

Dean nodded as best he could in his splayed-out position. It wasn’t comfortable, and for some reason the awkwardness of it made it even hotter. The fact that an audience of people could see into his wet, gaping hole had him hard all over again, cock hanging between his spread-out legs.

Katarina had blindfolded him, bent him over the bench, pushed his legs apart, locked the spreader bar in place at his ankles, and pulled out his plug all within the matter of seconds, with the same swiftness and confidence that Dean had when it came to changing oil in cars.

With his wrists attached to the cuffs at his ankles, he was free to put most of his weight on the bench, which was rounded with padded black vinyl, so it didn’t dig into his skin. Overall, he was pretty sure he would be fine like this for an hour. Benny had been putting him in much more taxing positions than this.

Katarina kissed the top of his head, ran her fingers through his sweat-damp hair. “Remember to safeword if you need to, Dean. I know you like toughing things out to make me proud, but know that my pride in you is unwavering, _si?”_

“Yes, Mistress,” Dean whispered, body relaxing even though he didn’t know he was tense.

Katarina put Anna in place next to him. When he heard the locks click, he wanted to ask her if she was okay, or tell her some kind of snarky joke, but he wasn’t sure if he was allowed to speak, so he remained silent.

The platform stopped vibrating as Katarina stepped off of it, and softly said, “You… and you.” Heavy, booted footsteps approached the platform and stepped onto it.

Dean could feel a soft brush of denim on the back of his thigh and heard the sound of a zipper being pulled down. A large, warm hand gripped his hip, and Dean could barely breathe.

Deep in his mind, something was telling him that he should have freaked out and safeworded, run away and never come back, but somehow he was perfectly calm; thrilled, even. He didn’t know who this guy behind him was, but he wanted to be fucked by him, wanted to feel him come in his ass, wanted to be used. It was some fucked up part of his brain that loved every second of being put on display.

A wrapper tore open, followed by the crinkling sound of lubricated latex. Beside him, Anna gasped and a man grunted, the sound of skin slapping against skin filling the air.

The blunt head of a cock pushed at Dean’s entrance and bottomed out none-too-gently. It burned in a way that made Dean’s stomach drop and forced a low groan out of his chest. The man behind him didn’t make a sound as he pulled out and slammed back in. The guy had no technique whatsoever, but Dean appreciated his fervor.

The dude blew his load in less than a minute, which Dean took as a compliment.

The next guy lined up, and Dean tensed in anticipation. His cock was hard and leaking, and he wished he could ask for it, beg for these men to at least aim for his prostate, but he knew that this wasn’t about his pleasure, it was about theirs, which made him so hot that his dick throbbed with the need to be touched.

The hands that rubbed up and down Dean’s back were thin and lithe with a soothing touch. The man fucked Dean gently and slowly, thrusting in and pulling all the way back out, over and over again, making sure to skate Dean’s sweet spot in the barest tease.

The man came at the four and a half minute warning that Katarina provided him, utilizing all thirty seconds to continue fucking into him through one of the longest orgasms Dean had ever experienced someone having.

Dean lost track of differentiating the participants after that. It was just a haze of blissful, throbbing subspace and unending pleasure; like nirvana, and Dean loved every second of it.

By the sixth, or maybe seventh or eighth, participant, Dean felt a set of strong, familiar hands on his back. He knew them because they were the roughest, most callused hands that he’d ever felt. They were hands that could pick him up like he weighed nothing and jerk him off in less than ten seconds. A cocky, huffed laugh was the only confirmation Dean needed that Benny was the next participant, confirmed further when the biggest dick yet stretched him open wider than anyone else had managed to.

Thank god Benny was a regular, because otherwise the size alone would have freaked him out enough to end the show. Dean was used to Benny’s cock though, was used to the careful way that he pushed into Dean, a slow, agonizing inch at a time. Dean gritted his teeth and gasped for breath as Benny stretched him wide. If they were in a normal scene, this was where Benny would say something like, “Fuck, you’re so tight. Can’t wait to open up that pretty little hole of yours,” Southern drawl clipped and panting.

Of fucking course, out of everyone who had fucked Dean thus far, Benny was the only one who reached around and fisted Dean’s cock, going from zero to a hundred in a matter of seconds. One moment, Benny slowly glided into him. The next, he was jacking Dean fast and hard and bottoming out in one smooth motion, only to pull out and slam back in.

Dean shouted and cut himself off from accidentally yelling Benny’s name.

Benny fucked him so hard the bench moved forward an inch, and Dean felt the weight of Benny’s massive chest lean on him as he kissed the back of Dean’s neck.

After what felt like hours, or maybe seconds, but what was actually only four and a half minutes according to Katarina’s thirty-second warning, Benny whispered behind a filthy chuckle, “I think you oughta come for me now, Dean.”

Dean’s orgasm immediately shot through him like Benny reached in and ripped it right out of his body with his big, rough hands. He came so hard that cum landed on his arms and in his hair and he just kept coming, until Benny finally followed behind him, slowing his thrusts with a quiet grunt. Dean could feel Benny’s massive cock throbbing with his orgasm, pulsing at the walls of Dean’s wet, fucked-open hole.

When his orgasm subsided, the second Katarina called time, Benny pulled out and Dean slumped even further on bench, body totally spent, but the next participant lined up and started fucking into him before he even caught his breath. His cock twitched in a valiant effort to get hard again, but all Dean could do was go pliant while the next guy pounded him for five minutes, and the next, and the next.

Even though his body felt like it was on the edge of breaking, and his mind was at the point where he couldn’t fathom pleasure anymore, he still knew that if he could, he’d do this every damn day of his life.

***

Castiel was not a jealous individual. Back in the day, he had dated Katarina while she had been married to a douchebag named Esteban. All parties involved were fine with it, and to Castiel’s knowledge, Esteban had a girlfriend on the side, too. Everything was happy until Esteban’s mother died and he had started beating Katarina through his mourning period. Cas tried to convince her to go to the police, but she refused, and the next thing he knew, Katarina was moving across the US and Castiel was reading Esteban’s obituary in The Times-Picayune.

Cas didn’t ask questions, and Katarina gave no answers.

When the putrid green bubble of jealousy burned in Castiel’s throat upon seeing Dean come on command by some bearlike, monster-cock oaf, Cas stood up from his chair and left the theater in a hurry. He could feel Katarina’s eyes on him as he left the room, likely that everyone else in the audience assumed he didn’t like jerking off in public. But Katarina knew better, and she’d be asking questions tomorrow.

None of the other men had bothered Cas, because Dean hadn’t come for any of them. He was just working. That was all this was: work. It wasn’t like what Dean and Castiel had, which was so much deeper and complex than anything else in Cas’s life to date.

As Cas ran up the spiral steps to the club floor and main exit, his heart raced at the speed of his thoughts. This was Dean’s _job_. Dean was paid to make Cas feel like they had a connection. Cas was just one of those creeps who developed feelings for sex workers, who got irrationally angry when their sad little bubbles burst that their one and only was actually available for purchase by other people.

It was all in his head. What happened between him and Dean at the club was like a coupon: Dean gave Cas free sex so Cas would keep coming back. Cas was good money, that was all. A steady paycheck. To boot, he was Dean’s lawyer too, so Dean was just double-insuring himself, making sure Cas would work his ass off for Dean in exchange for some false sense of… whatever he thought was happening between them.

How could Cas have been so _stupid._

He reached the exit and darted into the alleyway at the side of the building, chest heaving and hands trembling. He let himself lean against the wall and slide down it, press his forehead into his palms and squeeze his eyes shut.

A beautiful, intelligent, talented twenty-year-old could never love a lower-middle-class, rapidly-aging civil lawyer with six figures of debt who still managed to lose over half of his cases.

Castiel was _pathetic._

That man, the large one with the Southern accent, touched Dean like they knew each other, like they’d done it a thousand times before. There was familiarity in the man’s touch, care and compassion. Despite his enormous stature, he touched Dean more gently than anyone else had, and he fucked Dean differently too, put Dean’s pleasure before his own, so Cas couldn’t even hate him properly.

Cas couldn’t catch his breath. The ground spun beneath him, and he didn’t know how many minutes he waited there, drowning in his own panic.

Footsteps pulled him out of his reverie.

“Whoa there, brother, you feelin’okay? You’re white as a sheet.”

Cas looked up to find the enormous man who caused this whole problem staring down at him with open concern.

It was all too much: the case, Dean, the brothel, Katarina’s ceaseless yet oftentimes infuriatingly cold concern. He held her in such high regard that he was _angry_ with her for not being here to comfort him when he needed her. It was irrational. He knew it was irrational. Katarina had nothing to do with this. Hell, _Dean_ had nothing to do with this, not really. He was just a boy trying to make it by in a world that chewed him up and spit him out, like a beaten puppy who couldn’t find a home.

But this man, who looked at him like he was a real human being and not a pile of trash, who touched Dean with the same respectful regard, pushed Castiel over the edge.

Legality damned, Cas reeled his arm back and swung at the man with all of his weight, punch landing square across his jaw.

The man stumbled back, stunned, and put a hand to the side of his face. He took a deep breath and cracked his neck while muttering, “You gonna wish you hadn’t done that, brother.”

***

Dean left the brothel with a skip in his step, which may have had more to do with the sore state of his backside than his cheerful demeanor.

As he walked to his car, he heard crashing in the alleyway, grunting, and the distinct sound of someone using a blunt instrument to hit a slab of meat.

Because Dean lacked any modicum of sensibility, he approached the noise instead of heeding the nagging voice in the back of his head telling him to go get Katarina.

When Dean saw the shapes of two familiar individuals beating the ever-loving shit out of each other, he ran toward them.

Benny had Cas against a wall by his throat, and instead of punching him, he was open-faced slapping him, repeatedly, boxing his ears until Cas looked like he was barely conscious, all the while speaking calmly, “I know you’re having a bad night, brother, but that don’t mean you get to take it out on innocent bystanders.”

“Benny!” Dean pulled at his bicep and yanked him away, but it was as effective as trying to pick up an eighteen-wheeler with his pinky finger. “Benny! Stop it! He’s not even fighting back anymore!”

Again, Dean might as well have been a goddamn mosquito.

“I’ll call the cops!”

Nothing.

Finally, Dean shouted, _“IMPALA!”_

 _That_ got Benny’s attention, and he whipped his head around while letting go of Cas and stepping away, hands lifted.

“Dean,” Benny said, breathless, looking onto the scene like he’d just arrived.

Dean noted the nasty-looking bruise on the side of his face, but dropped down to Cas’s side, who was bleeding from several places, jaw slack, eyes rolling into the back of his head. He looked up at Benny and asked, “What the hell did you do?”

Benny shrugged and put his bloodied hands in his pockets, casual and guilty, like Dean was chastising him for spilling milk and not for beating the crap out of Dean’s client-lawyer-pseudo-boyfriend. “He attacked me.”

“Cas?” Dean whispered, looking down. He brushed Cas’s hair away from his forehead, wiped some blood off of his mouth. “Is that true?”

Cas nodded, a fraction of a movement, and Dean went cold.

“Why?” Dean asked, barely above a whisper.

With a pained groan, Cas replied, “You.”

Dean held up Cas’s weight and rifled through all of Katarina’s rules for something to help handle this situation.

Benny squatted down to his level and touched his shoulder gently. “Listen, brother. You know I have nothing but the utmost respect for you and the work you do, but there are always gonna be those,” he snarled at Cas, _“clients_ who think the service you provide is more than just a service, you hear? And they’re gonna get possessive when they see you provide that same service to others. You want my advice, you’ll go get Katarina to make sure this fella don’t come back.”

Dean looked away and nodded, jaw clenching while his chest tightened.

“Now, you’re just lucky this fella attacked me and not someone who woulda pressed charges on him and Katarina and her whole operation. In fact, you ain’t even gonna lose me as a client. I know this business, Dean, and I know the dark side of it, too.” Benny stood and concluded, “I’ll see you next week, brother.”

“Yeah, Benny. See you next week,” Dean replied, voice wavering.

Benny walked away, hands in his pockets, whistling like nothing even happened.

Dean wrapped Cas’s arm around his shoulders and hauled him up. “C’mon, Cas. I’ll take you back to my place so we can figure this out before we face Katarina’s wrath.”


	8. Chapter 8

**Notes for the Chapter:**

> IT IS DONE.
> 
> Chapter beta'd by the utterly fucking glorious [B&E](http://www.bert-and-ernie-are-gay.tumblr.com), who is SITTING IN THE SAME ROOM AS I AM RIGHT THE FUCK NOW HOLY SHIT.

The ride to Dean’s apartment was mostly silent, but Dean continued stealing glances out of his peripheral vision.

Cas was slumped over, head resting against the window, eyes closed. He was bleeding from a cut on his head, and he was bruised to shit, but otherwise he didn’t look too bad. Not hospital-bad, at least.

Cas broke the silence by mumbling, “Nice car.”

Dean huffed a laugh and replied, “Thanks. It was my old man’s.”

After a pause, Cas asked, “What was he like?”

No one asked Dean about his father anymore. It hadn’t even been a year since he died, but already it was like he never lived, like the only people who knew him were Dean and Sam.

Dean bit absently at his thumbnail, drove with one hand on the steering wheel, a small smile crossing his face as he flitted through memories of his father. “He wasn’t a great dad, but he was a good man. Tough, strong. Drank too much. Swore too much. Told the same stories over and over again. Demanded respect without doing anything to earn it.”

From the corner of his eye, Dean could see Cas nod and shift in his seat, wince in pain and settle again.

“What’s your dad like?” Dean asked.

Cas shrugged. “Haven’t seen him in a long time. Back when he was around, he was a drugged-up hippie dating a woman younger than me. The man hasn’t had his shit together a day in his life. Could be dead for all I know. Or in Amsterdam.”

Dean risked a full glance over at Cas. “So how’d you end up so—“

“Broken?”

“No, I was going to say successful.”

“Oh.”

Dean reached out and grabbed Cas’s hand, lying limply at his side, pulling it closer to him and threading their fingers together.

Cas looked out the window and replied, “I don’t see how you could possibly see me as successful. You know—” Cas trailed off with a sigh. He continued after a moment, quietly, “You know the case isn’t looking good, Dean.”

“I know,” Dean replied, and even though he should have been nervous, should have been clawing at the walls in dread, he wasn’t. He trusted Cas, even if Cas couldn’t trust himself. The person he was at his core was the man Dean loved with all his heart, the man in whom he had unyielding faith. “I mean, if we’re measuring success here, I’m a twenty-year-old high-school dropout who can barely keep a roof over his head. And you’re….” Dean trailed off, throat suddenly constricting.

“I’m what?” Cas asked, hesitant, sitting up and squeezing Dean’s hand again.

Dean shook his head. “I don’t know, man. You’re the only one out there who gives a damn about me and my brother. I sell my body to you and you still respect me, still see me as a person, when no one else in this whole fucked-up world would. You bust your ass for me, for _us_ , for my little broken family when I don’t…I don’t even deserve someone like you, Cas.” Dean took in a deep, shaking breath and couldn’t bring himself to say anything else.

Cas picked up Dean’s hand and brought it to his lips, gently kissed his wrist and whispered against it, “You do, though, Dean. You deserve everything good this world has to offer.”

Thankfully, they arrived at Dean’s apartment before his eyes could become obscured by the tears threatening to flood his vision.

Cas let go of his hand and Dean put the car in park, but didn’t bother turning off the ignition before reaching over and pulling at the lapel of Cas’s trench coat, dragging their lips together. Dean was careful of the bruises, but Cas still deepened the kiss, ran his fingers through Dean’s hair and gripped it, a soft, desperate groan escaping his throat.

Dean maneuvered himself so that he could crawl into Cas’s lap, straddle him at the thighs and kiss him until they were both breathless, panting at each other’s mouths and expressing through touch all the things they had left to say to one another.

Dean had already come earlier in the evening more times than he could count, but the itching, writhing need that crawled blissfully under his skin whenever he was around Cas, whenever he was kissing Cas, whenever he could smell Cas’s musky, male scent of aftershave and soap and a too-long day of work (which was probably all Dean’s fault),—that need left him aching and hard and wanting to go a hundred more rounds.

“Dean,” Cas said, exhaling a moan that barely shaped his name as he ran his hands up the back of Dean’s t-shirt and dragged his nails down.

Dean hitched his hips and a thrill ran up his spine when he felt Cas hard too, and this was so fucked up, dry-humping his lawyer with whom he was horribly in love in the front seat of his car after having the shit beat out of him by a dom who was only one in line out of a dozen to fuck Dean earlier that night in front of an audience.

But all of it—from the windows fogging up, to the door handle pressing into the side of his thigh, to the dull ache of his ass—every moment was perfection, and if Dean didn’t realize how much he missed Cas before, he realized it now, hips grinding faster and harder while Cas bucked up against him, kissing and sucking at Dean’s throat, one hand on the back of his neck while his other gripped his hip.

“Cas,” Dean began, broken and ragged like a rotting prayer, “I’m gonna….” He didn’t know how it was possible that the burning pressure building at the base of him could grow so quickly after a night like tonight, but Cas had always been able to do this to him, get him to respond to the slightest feather touch.

Cas mouthed at his throat, reached up his shirt to flick a nipple with his thumb, and whispered, “I want you to come for me, Dean. Just like this.”

Dean’s body went rigid, and Cas rolled his hips once more, skating over Dean’s clothed cock with his own, and Dean came, hard and fast, groaning out, _“Fuck,_ Cas. Fuck fuck _fuck_ ,” hot spurts of fluid filling his boxers and trailing down the crease of his thigh as his cock continued twitching against his jeans, looking for more friction.

Cas gripped Dean’s hips hard enough to leave bruises and shoved Dean down onto him, stopping frozen with a sharp intake of breath that exhaled into a deep moan as he dropped his head on Dean’s chest. Dean could feel Cas’s cock throb underneath him with every wave of his orgasm, heat pooling at the inside of Dean’s thigh.

Dean kissed the top of Cas’s head and asked, “I think we did this in the wrong order, but…do you wanna come inside?”

Muffled in Dean’s chest, Cas replied, “I already did.”

Dean laughed and crawled out of Cas’s lap to turn off the car. “C’mon. I’ll get you an icepack for your face.”

When Cas didn’t move, head lolled back against the seat, breathless, Dean climbed out of the car and walked around it, opened the passenger door, and pulled at Cas’s arm.

Cas groaned, “I’m not twenty years old anymore. I can’t come and immediately bounce back up for round two.”

“There’s gonna be a round two?” Dean asked, eyebrows raised.

Cas eyed him while taking his hand to climb out of the car.

***

Dean’s apartment was pretty much what Castiel had been expecting: small, messy, filled with secondhand furniture, yet still cozy.

Cas took a seat on the lumpy orange floral couch while Dean tossed his leather jacket on the back of a chair and went into the bathroom, mumbling something about a first-aid kit. While Cas waited, he leaned forward to inspect a pile of books under the coffee table.

There were a stack of paperback library novels of wide variety, from classic sci-fi to modern mystery. The one on top— _Player Piano_ by Kurt Vonnegut—had a McDonald’s receipt stuck in the middle of it. Cas opened it and skimmed over a passage:

_In order to get what we've got, Anita, we have, in effect, traded these people out of what was the most important thing on earth to them—the feeling of being needed and useful, the foundation of self-respect._

Dean came back in the room, set the first-aid kit on the table, and knelt by Cas’s feet.

Cas set the book back down and asked, “You…enjoy reading?”

Dean huffed a laugh while he opened the kit. “Don’t sound so surprised.”

“I’m not. You just…seem too busy for it.”

Dean shrugged and picked up a wet cloth he’d brought in a bowl, reached up and cleaned the cut on Cas’s forehead. “I read fast,” he replied absently, and all the while Cas stared into his beautiful green eyes, at his parted lips, plush and wet and red with Cas’s own stubble burn.

The kneeling, the tender care of Dean’s touch, the sheer hopelessness of their cause made something churn deep in Cas’s gut.

Cas took Dean’s hand away from his forehead to get his attention, held his wrist in his hand and looked him in the eye. “Dean…” he began, and trailed off, averting his gaze.

“What?”

Cas shook his head. “You should be upset with me. I acted…rashly tonight. Stupidly. You shouldn’t be helping me right now.”

Dean tugged his wrist away and continued dabbing at Cas’s forehead. “Don’t be ridiculous.” He finished with the cloth and set it down, picked up a tube of Neosporin and squeezed some onto a Q-tip. As he spread it over the cut, he added, “Plus there’s no reason for me to be mad at you when Benny seemed to have taught you a lesson anyway.”

Cas winced at the sharp sting of the ointment and replied quietly, “Benny was right, you know.”

“About what?”

“ _Me_. I’m the worst kind of cli—”

“We don’t use that word anymore, remember?” Dean interrupted tersely, ripping open a band-aid.

“Still, I’ve…I’ve never done this before. This—” He gestured between them. “Whatever this is, and I’m handling it poorly because I’m…worried it’s all in my head,” he concluded, rushing through the end of the sentence until it came out as a rough mumble.

Dean opened his mouth to reply, but Sam walked into the living room, backpack on his back, looking at them in confusion.

“Mr. Novak?” he asked.

Dean quickly put the band-aid on Cas’s head and stood up, picking up the items from the table. “Heya, Sammy. Where you headed?”

“I’m staying at Kevin’s house tonight,” he explained slowly, eyes narrowed.

Cas waved at him and gave him a wan smile.

“Why is Mr. Novak here?” he asked as Dean walked by him into the kitchen.

“Well, um….” Dean began.

“I got into a car accident,” Cas explained. “Dean happened to be there and offered to bring me here….”

“Because it was closer,” Dean completed. “Than Cas’s apartment.”

A horn honked outside, and Sam walked to the front door, saying, “I gotta get going, Kevin’s mom’s outside.”

“Hold up,” Dean said. “Why’re you leaving so late?”

Sam shrugged. “Kevin had a cello concert and his mom offered to pick me up after. We have a debate challenge tomorrow.”

“Oh. Well. Have fun, then. Do you have Dad’s phone?”

Sam opened the front door and rolled his eyes. “Yes, Dean. I’ll call you tomorrow. Nice seeing you again, Mr. Novak. Sorry about your accident.”

Cas nodded and Sam left. Dean called after him, “Good luck at your debate thing!”

After Sam made it down the stairs and outside, Cas stood, groaning in pain. Dean crossed back around the counter to steady him at the ribs, take his chin in hand and kiss him gently. “This isn’t in your head, Cas. I promise.”

Overcome with exhaustion, Cas couldn’t manage more than resting on Dean’s shoulder, wrapping his arms around his waist. He let himself, even though he knew he shouldn’t, that in a matter of days he would be facing Dean in a courtroom asking him questions, having to look into those same eyes and pretend they were virtual strangers.

But that was later. Right now, he had Dean in his arms, and they were safe and alone.

For now, he reminded himself. He had no idea how Katarina was going to react, but Esteban’s obituary floated through his head.

Dean let go and took a step back. “You want to take a shower? Maybe come to bed with me after?”

Cas nodded into Dean’s shoulder, and Dean took his hand, led him into the bathroom to shed their clothes and step into the warm spray. The water stung the cuts over Cas’s face, but Dean kissed all of the bruises, ran soapy hands over Cas’s tired body. It was like being cleansed, baptized, purified of the moral ambiguity inherent in working within the US justice system.

Cas let himself be cared for, even though he didn’t deserve any of it. He let Dean worship and soothe him, too tired to do much else but kiss Dean and hope it said for him all the words he couldn’t.

When the water ran cold, Dean rinsed them and turned it off, offered Cas a towel and a pair of sweatpants, and guided them into Dean’s bedroom.

Like the rest of the apartment, it was small; the only furnishing in it was a crate with a lamp on it and an air mattress on the ground.

Dean rubbed the back of his neck. “Sorry, it’s all I’ve got.”

Cas took his hand and laid them down, covered them with an old quilt, and kissed Dean until all his sorrows were gone, legs tangled and arms wrapped around each other. The kisses slowed until Cas began drowsing between each one, waking up to place another on Dean’s lips, again and again, until they finally fell asleep.

***

Dean was startled awake by a loud banging on his front door. “What the—“

Cas fell out of the bed, blankets wrapped around his legs, and Dean jumped to his feet, pulling on a pair of sweatpants and hopping into the hallway to yank them up to his hips, yelling, “Just a minute!”

When he finally reached the front door, he flung it open to find Katarina, eyes aflame and staring up at him in a fury. She pushed past him gracefully and strode into the apartment, turning on her heel and hissing out rapid Spanish, arms flailing.

Dean backed away, hands raised in front of him in a helpless gesture, and Katarina continued forward until he was cornered. She wore a long black trench coat and high-heeled boots, a large pair of sunglasses perched atop her wavy black hair.

Voice breaking like a fourteen-year-old, Dean shouted, “Cas! You have a visitor!”

Cas fell out of the bedroom, zipping up his pants, his white button-down shirt open as he rushed into the living room.

Katarina rounded on him, never taking a breath as her voice rose louder and louder, approaching Cas until her finger was prodding his bare chest, spitting out words that Dean couldn’t even begin to parse out.

“Katarina,” Cas pleaded, hands up. She was undeterred.

“It’s not what you think,” Cas spoke over her, eyes squeezed shut.

“Then what is it, Castiel?” she hissed, finally switching to English. “What is it that would cause you to accost one of my best clients on my property? Do you have any idea what kind of damage you could have caused my business? What kind of damage you would have caused me?”

Dean watched, frozen in place. Cas gulped, eyes wide, and shook his head slowly, “I don’t…I’m sorry, Katarina. I don’t know what came over me. Things have been so—“

“Excuses!” Katarina interrupted. “Do not fool me, Castiel. I have known you many years. I did not think you capable of this. I thought you were an angel.”

Dean took a deep breath and stepped forward. “It’s my fault, Katarina.”

“Dean, no,” Cas began, but Dean cut him off.

 “No, it’s my fault. I knew what was happening and I didn’t do anything to stop it. I egged Cas on. I broke your rules. I broke the state’s rules. I was selfish. I just… I wanted… I don’t even know.”

Katarina turned toward Dean, lips set in a hard line. She shook her head, tense shoulders rounding and face softening. “No, _mi amor_ , you are young, you are grieving, you are learning. You did not attack an innocent man. You broke my rule of seeing a client outside of my permission, and we will discuss that later, but for now, I will not let you take the blame for a fallen angel’s offenses.”

Cas fell into a dining room chair, head buried in his hands.

Katarina took a seat next to him and pulled his hands away from his face. “Castiel,” she said with a deep, steadying breath, tone softer but still clipped. “I am giving you the opportunity to explain yourself.” The _before I exact your punishment_ , Dean thought, was implied.

Cas hung his head, letting Katarina hold his hands. From where he was standing, the light of early morning sun streaming through the blinds of his living room, Dean could see small, bloodied spots dotting Cas’s knuckles.

“I don’t know,” Cas began, smaller than Dean had ever seen him, this larger-than-life man reduced to a rumpled mess under Katarina’s exacting yet forgiving gaze. “Is dom drop even a thing?”

 _“Si,”_ Katarina replied, barely above a whisper.

“I just….” Cas looked up at Dean briefly before averting his eyes again. “I saw Dean at the show, and I lost it. I’ve never felt that before. And I….” He dropped his head, and his shoulders shook silently, head shaking back and forth, voice breaking. “I love him.”

Dean’s breath caught in his throat, and he fell against the wall, sliding down it like he’d been shot. His heart physically ached in his chest, and when he looked up, Cas was staring at him over Katarina’s shoulder, eyes glistening and jaw clenching. “I love him,” he repeated, like a chant, like every time he said the words, it filled them with more truth.

Katarina replied quietly, “Love must not be something we possess. It must be something that possesses us. Do you understand?”

Cas nodded.

She reached forward and caressed Cas’s face, lifted his chin so that their eyes met. “Can you promise me you will no longer confuse body and heart?”

He kept her gaze as he replied, “Yes, Mistress.”

She kissed his forehead and whispered with a small smile, “You are a light in this dark world, Castiel. But you must find your grace again. I hope Dean will be able to guide you.”

Katarina stood, and Cas followed. “So you’re not going to fire Dean? Or ban me from the brothel?”

She walked toward the door and reached out a hand to Dean. “Dean will be my employee as long as he continues finding solace in his work.”

Dean took her hand and stood, at last finding his voice. “But will Cas continue to be my…?”

Katarina opened the front door and hesitated in the threshold. “Would you like Castiel to be your client, or would you like him to be more?”

“More,” Dean replied without hesitation.

“Then I see no problem with you seeing each other outside of my place of business, however, I feel that Castiel should take some time away.” She winked at Cas. “But I have a feeling that will not be a problem.”

Katarina left the apartment, closing the door behind her.

Dean stared at it a moment before turning back to Cas.

Cas rubbed the back of his neck, other hand in his pocket.

Dean asked, barely believing the words escaping his lips, “You love me?”

Cas nodded. “I do, yes. I’m sorry if…if that’s unwelcome. I read about this happening a lot, when cli—“

Dean surged forward and kissed him before Cas could finish his sentence, chest wrenching so forcefully that tears stung the corners of his eyes.

Cas grasped at him, drank him in greedily, a clash of lips and bodies; desperate, breathy groans filling the air between them.

Dean broke the kiss and pressed his forehead to Cas’s, eyes squeezed shut. “You’re not my client anymore.”

Cas huffed a laugh. “After Monday, you won’t be mine either.”

Dean intertwined their hands together, fingertips grazing the scabs of Cas’s knuckles, grinning so widely he thought his face might break. “Breakfast?”

Cas pressed his lips to Dean’s once, quick and chaste. “Breakfast.”

***

Dean wasn’t sure what he was expecting when he was initially told he would have to go to court, but it didn’t involve sitting on an uncomfortable bench with his face in his hands, trying his damnedest not to hyperventilate.

He supposed he was expecting something more akin to _Law & Order_, but when he muttered as much, Sam laughed at him.

Even when he’d been in the courtroom, it involved mostly yes-or-no or short-answer questions, which he replied to, ending each answer with, “sir.”

He was sure he wasn’t imagining the heat behind Cas’s eyes, nor the way he clenched his jaw, nor the pointed way he avoided Dean’s gaze.

Dean had gotten hard after the third question, but thankfully Cas had briefed him so well that Dean could go on autopilot and only had to subtly shift himself into his pantleg once.

Everything was _so_ fucked.

Sam patted Dean’s shoulder.

“How the hell are you so calm about this?” Dean asked, muffled in his hands.

He could feel Sam shrug next to him. “Mr. Novak seems like he knows what he’s doing.”

Dean groaned.

The door to the courtroom opened and Cas stepped out, face stern.

Dean stood, eyes wide, barely breathing. Sam followed, hovering behind Dean’s shoulder.

Cas stared at them for a brief moment, face utterly blank, before breaking into a grin and exclaiming, “We won!”

Dean spun around and wrapped his arms around Sam. Sam squeezed him so tightly he thought his ribs might break.

Dean’s chin trembled, tears flooding his vision which cascaded down his face as he let out a shaking laugh. As he let go of Sam, he wiped his face with the back of his hand, sniffled, and turned back to Cas. He lifted his arms, but dropped them again and instead held out a hand. “Thank you…Mr. Novak. For everything.”

Cas smiled, looking lighter than he had in weeks, and shook Dean’s hand. “It was my pleasure, Dean.” He patted Sam on the shoulder before picking up his briefcase and adding, “I’ll contact you soon for a follow-up, make sure everything is going okay.”

“Sounds great,” Dean replied, trying to keep his face from breaking open, from dropping to his knees and sobbing with happiness and relief.

Sam turned to pick up his backpack, and Cas winked at Dean once before leaving the courthouse.

***

Cas lit a candle on his dining-room table as the doorbell to his apartment rang.

He set the lighter down and rubbed his sweaty palms on his slacks before walking to the front door and opening it.

Dean stood there, a small smile playing on his lips and a blush on his cheeks, plaid shirtsleeves rolled up to his elbows and wearing what Cas knew to be his only pair of jeans without holes in the knees.

“Hello, not-client,” Cas said, grin widening.

Dean huffed a laugh and grinned back. “Hey, not-client.”

Cas moved aside and gestured Dean in. Dean entered and looked around. “You got a nice place.”

“Thank you,” Cas replied stiffly, shutting the door and walking into the small dining room adjacent to the similarly-sized kitchen.

“Smells good, too.”

“Dinner’s ready on the stove. Can I get you anything to drink?”

Dean stepped into his personal space and slid his hands onto Cas’s hips. “I don’t know. I thought this was a business meeting. You know, to check up on me, make sure I’m doing okay.”

Cas looked down, hiding his smile and laughing. He flitted his eyes back up and met Dean’s gaze. “How are you doing, Mr. Winchester? Everything alright at home?”

“Everything’s great,” Dean replied with a shake of his head, and leaned in to add, “… _Master_.”

Cas swallowed audibly, smile dropping as he took Dean’s hands, crowded his body up against the door and kissed him like there was no tomorrow.

As he trailed open-mouthed kisses down Dean’s neck, Dean asked, voice tight, “What about dinner?”

Cas growled against his throat, unable to contain himself any longer after almost an entire week apart, “Fuck dinner.”

It’d been the longest week of his life, every nerve underneath his skin firing, wanting Dean for what had felt like an eternity. “Need you,” he added, ragged, hiking Dean’s shirt up and skirting his hands underneath, feeling the blissful expanse of skin and muscle underneath his palms.

“Jesus, Cas,” Dean replied, breathless, hitching his hips against Cas, small noises escaping his throat.

Cas hooked two fingers in Dean’s belt loop and pulled, dragging Dean behind him into the bedroom.

“I thought this was supposed to be a date,” Dean said flippantly as Cas shoved him inside, pushing him back onto the bed. Cas straddled his hips and kissed him again, biting at his bottom lip and hiking Dean’s shirt up to his chest. “What happened to the _reserved_ dom I first—“ Cas thumbed over his nipples and Dean arched his back, hissing out, _“Fuck,_ Cas.”

Cas popped open the button of Dean’s jeans, reached down into his pants and grabbed his cock, fisting it in quick, hard strokes. Dean gasped and let out a loud moan, fucking instinctively into Cas’s hand as he twisted his fingers into the sheets.

Cas laved at his neck, slicking up his palm with the precum already flowing out of Dean, jacking him until Dean panted out, “Cas, _fuck_ …I’m gonna come already, Jesus fucking Christ, your _hands_.”

Cas gritted his teeth and forcibly slowed his movements, stroking the entire length and twisting at the tip, panting into Dean’s open mouth.

Dean’s breath evened out and he let out a small groan with every exhale, grasping at Cas’s back until he untucked Cas’s shirt from his pants, reached down them and pressed the flat of his fingertip to his hole.

Cas’s brain erupted in pleasure and he fucked against Dean’s hip, pressing back against his hand, taken so off-guard that he pulled his hand out of Dean’s pants to steady himself on the bed, and Dean flipped them over.

Cas bit his lip and stifled a groan as Dean unbuttoned Cas’s shirt so quickly that several buttons flew off, and he leaned down to kiss down Cas’s chest to the trail of soft, dark hair leading into his slacks.

With the same swiftness, Dean pulled down Cas’s pants to his hips, freeing his leaking, throbbing cock. Cas let go of him as Dean leaned back to yank his own shirt over his head and quickly kick off his pants and boxers until he was gloriously naked, lithe muscles and freckled skin lit only by the light coming through the crack in the door.

Dean leaned back down, kissing Cas deep and slow, and Cas reached behind Dean, ran his fingers down his crack and circled his hole, finding it already open and slick. He let out a low groan as he easily sank two fingers inside.

“God… _Dean…”_ Cas groaned, fucking his fingers in and out until Dean was panting at his collarbone, pushing back onto Cas’s fingers with abandon, providing the barest amount of friction, cocks dragging against each other. The thought of Dean fucking himself open with a toy in preparation for tonight flitted through Cas’s mind and put him on edge as he scissored his fingers and opened Dean up wider.

Muffled, between gasped breaths, Dean begged, “Please, Cas…let me ride you. _Please.”_

Cas nodded, completely unable to speak, and pulled his fingers out. Dean scrambled to straddle his waist as Cas grabbed a condom from the bedside table, ripped it open, and rolled it over himself.

Dean grabbed Cas’s cock in hand and lined himself up, sinking down onto it slowly. Cas could feel his cock throb as Dean’s jaw went slack, the rim of his ass pulsing as it stretched, eyes fluttering shut as he inched further down until Cas was seated fully inside of him.

They caught their breaths together as Dean adjusted to Cas’s girth, and Dean leaned down, kissing him gently, slowly. He pulled away, just an inch, and lifted himself off of Cas’s dick to sink back down. Cas let out a deep exhale and writhed underneath him.

Peppering his lower lip with kisses, Dean asked, barely above a whisper, “You know I love you too, right?”

That was it. Cas was gone, drowned in Dean’s affections, hands moving of their own volition as he threaded his fingers in Dean’s hair, gripping it, other hand on his hip, fucking up into Dean instead of answering, because there was no answer to give but the need for _more_ , bodies pressed together, slick with sweat and Dean’s cum pooling between their stomachs.

They met in a rhythm, and Dean angled his hips slightly so that the tip of Cas’s cock grazed his prostate on each thrust until Dean was gasping for breath, biting onto Cas’s shoulder, fists balled into the sheets at either side of Cas’s head.

Cas steadied his grip on Dean’s hips and continued fucking into him, reaching between them to take hold of Dean’s cock and flick at the head with his pad of his thumb, sweep it back down and jack him in time with their movements.

“Fuck, Cas….” Dean panted. “So close.”

Cas still couldn’t speak, mind obliterated of everything but the feel of Dean riding him, so he nodded into Dean’s shoulder, speeding up his thrusts until his hips slapped against Dean’s ass.

Dean went still, breath shallow and ragged, hanging on the precipice.

Cas fucked into him once more, hard and deep, and Dean came with a sharp intake of breath, hot cum flowing between their stomachs and chests, asshole clenching around Cas’s cock until Cas came right behind him with a strangled cry, cock settled deep inside of him as his shuddering hips slowed to a halt.

He felt Dean’s heart beat against his chest, leaving soft kisses down his neck with small moans escaping his throat.

Dean lifted off of Cas and rolled to the side of him, collapsed together. Cas’s pants were still caught at his hips, his shirt open and covered in cum as it slid down the side of his stomach.

“What happens now?” Dean asked, breathless.

Cas managed a shrug as he pulled his pants up to his waist. “Dinner. Or sleep. Preferrably sleep.”

Dean huffed a laugh against his shoulder. “I mean…us. Do you want me to quit the brothel?”

With reluctance, Cas sat up on his elbow and stared down at Dean. “What? Why would I do that?”

Dean averted his eyes as he replied, “I dunno. Benny, I guess. And, you know, that’s kind of how these stories always end.”

Cas leaned down and kissed him, reveling in the sweet, wonderful taste of him before replying, “Dean, please be honest with me. Money aside, do you enjoy working for Katarina?”

Dean hesitated for a moment, and gave a slight nod.

“Then that’s what’s important. You’re doing something you enjoy, something that you’re, _fuck_ , amazing at, in a safe environment. I promised Katarina I wouldn’t let what happened happen again, and I intend to keep that promise. I want you to do what you think is best.”

Dean bit his bottom lip before asking, “But you’re not, like, ashamed of me? Having a twenty-year-old sex worker boyfriend?”

Cas smiled at the term and kissed him again, because he just couldn’t help it. “There is nothing shameful in what you do, and I’m proud of how much you’ve been able to achieve already.”

Dean nodded in contemplation, and concluded, “I want to keep working for Katarina.”

“Then I also want you to keep working for Katarina.” After a short pause, Cas added, “And I’m sure that’s what Katarina wants too.”

“So….” Dean began, “Are you going to keep…hiring other workers?”

Cas shook his head and hugged Dean closer. “No, I think I’m done being a patron at _La Casa de la Diversión_.”

As if on cue, Dean’s phone beeped in his pocket, and he stood up with a broken noise to fish it out of his pants, discarded on the ground. Dean pressed a button and read the message, then gave a short reply and tossed the phone onto the bed before grabbing some tissues, climbing back in, and settling against Cas, cleaning off both of their stomachs.

“Who was that?” Cas asked.

“Katarina,” Dean mumbled, tossing the tissues away, breath already evening.

“What’d she want?”

“Me to work the club tonight.” Dean buried his face in Cas’s chest, entwining their legs together. “Told her tomorrow,” he slurred, eyelashes fluttering shut against Cas’s neck.

Cas kissed the top of Dean’s head, enjoying the feel of Dean’s heart beating, as they both drifted off to sleep.


End file.
